Thieno-indeno-monomers and polymers

ABSTRACT

Disclosed herein are polymers comprising at least one unit of formulae (1a)-(1f):

The present invention relates to new monomers and polymers made thereof,in particular thieno-indeno-monomers and polymers, to a process for thepreparation of these monomers and polymers, to intermediates, toelectronic devices comprising these polymers, as well as to the use ofthese polymers as semiconducting material.

Organic semiconducting materials can be used in electronic devices suchas organic photovoltaic devices (OPVs), organic field-effect transistors(OFETs), organic light emitting diodes (OLEDs), organic photodiodes(OPDs) and organic electrochromic devices (ECDs).

It is desirable that the organic semiconducting materials are compatiblewith liquid processing techniques such as spin coating as liquidprocessing techniques are convenient from the point of processability,and thus allow the production of low cost organic semiconductingmaterial-based electronic devices. In addition, liquid processingtechniques are also compatible with plastic substrates, and thus allowthe production of light weight and mechanically flexible organicsemiconducting material-based electronic devices.

For application in organic photovoltaic devices (OPVs), organicfield-effect transistors (OFETs), and organic photodiodes (OPDs), it isfurther desirable that the organic semiconducting materials show highcharge carrier mobility.

For application in organic photovoltaic devices (OPVs) and organicphotodiodes (OPDs), the organic semiconducting materials should alsoshow a strong absorption of the visible light.

It was the object of the present invention to provide organicsemiconducting materials. This object is solved by the polymers of theinvention, a process for preparing the polymers, intermediates forpreparing the polymers electronic devices containing the polymers andthe use of the polymers.

The polymers of the present invention comprise at least one unit offormula

Also part of the invention are compounds of the formulae

wherein, in formulae 1, 1′, 2 and 2′

n is 0, 1, 2, 3 or 4

m is 0, 1, 2, 3 or 4

M1 and M2 are independently of each other an aromatic or heteroaromaticmonocyclic or bicyclic ring system;

X is at each occurrence selected from the group consisting of O, S, Seor Te, preferably O, S or Se, more preferably S or Se, most preferablyS;

Q is at each occurrence selected from the group consisting of C, Si orGe, preferably C or Si, most preferably C;

R is at each occurrence selected from the group consisting of H,C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl, C₂₋₁₀₀-alkynyl, C₅₋₁₂-cycloalkyl,C₆₋₁₈-aryl, a 5 to 20 membered heteroaryl, C(O)-C₁₋₁₀₀-alkyl,C(O)—C₅₋₁₂-cycloalkyl and C(O)-OC₁₋₁₀₀-alkyl,

-   -   wherein    -   C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl can be        substituted with one to fourty substituents independently        selected from the group consisting of C₅₋₈-cycloalkyl,        C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(a), OC(O)—R^(a),        C(O)—OR^(a), C(O)—R^(a), NR^(a)R^(b), NR^(a)—C(O)R^(b),        C(O)—NR^(a)R^(b), N[C(O)R^(a)][C(O)R^(b)], SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), —O—Si(R^(Sia))(R^(Sib))(R^(Sic)),        halogen, CN, and NO₂; and at least two CH₂-groups, but not        adjacent CH₂-groups, of C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and        C₂₋₁₀₀-alkynyl can be replaced by O or S,    -   C₅₋₁₂-cycloalkyl can be substituted with one to six substituents        independently selected from the group consisting of C₁₋₆₀-alkyl,        C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to        14 membered heteroaryl, OR^(a), OC(O)—R^(a), C(O)—OR^(a),        C(O)—R^(a), NR^(a)R^(b), NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b),        N[C(O)R^(a)][C(O)R^(b)], SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, CN, and NO₂; and one        or two CH₂-groups, but not adjacent CH₂-groups, of        Cs-12-cycloalkyl can be replaced by O, S, OC(O), CO, NR^(a) or        NR^(a)—CO,    -   C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted        with one to six substituents independently selected from the        group consisting of C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,        C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,        OR^(a), OC(O)—R^(a), C(O)—OR^(a), C(O)—R^(a), NR^(a)R^(b),        NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b), N[C(O)R^(a)][C(O)R^(b)],        SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, CN, and NO₂,        -   wherein        -   R^(a) and R^(b) are independently selected from the group            consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl,        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl,            C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered            heteroaryl, O—C₁₋₆₀-alkyl, O—C₂₋₆₀-alkenyl, O—C₂₋₆₀-alkynyl,            O—C₅₋₈-cycloalkyl, O—C₆₋₁₄-aryl, O-5 to 14 membered            heteroaryl, —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif), NR⁵R⁶,            halogen and O—C(O)—R⁵,            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie), R^(Sif) are independently selected                from the group consisting of H, C₁₋₆₀-alkyl,                C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl,                C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, O—C₁₋₆₀-alkyl,                O—C₂₋₆₀-alkenyl, O—C₂₋₆₀-alkynyl, O—C₅₋₈-cycloalkyl,                O—C₆₋₁₄-aryl, O-5 to 14 membered heteroaryl,                —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii), NR⁵⁰R⁶⁰, halogen and                O—C(O)—R⁵⁰;                -   wherein                -   p is an integer from 1 to 50,                -   R^(Sig) R^(Sih), R^(Sii) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, O—Si(CH₃)₃, NR⁵⁰⁰R⁶⁰⁰, halogen and                    O—C(O)—R⁵⁰⁰,            -   R⁵, R⁶, R⁵⁰, R⁶⁰, R⁵⁰⁰ and R⁶⁰⁰ are independently                selected from the group consisting of H, C₁₋₆₀-alkyl,                C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl,                C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl,            -   C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and C₂₋₆₀-alkynyl can be                substituted with one to twenty substituents selected                from the group consisting of C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)R^(d), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), N[C(O)R^(c)][C(O)R^(d)], SR^(c),                Si(R^(Sij)(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, CN, and NO₂;                and at least two CH₂-groups, but not adjacent                CH₂-groups, of C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and                C₂₋₆₀-alkynyl can be replaced by O or S,            -   C₅₋₈-cycloalkyl can be substituted with one to five                substituents selected from the group consisting of                C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c),                C(O)—OR^(c), C(O)—R^(c), NR^(c)R^(d), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), N[C(O)R^(c)][C(O)R^(d)], SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij)(R^(Sik))(R^(Sil)), halogen, CN, and NO₂;                and one or two CH₂-groups, but not adjacent CH₂-groups,                of C₅₋₈-cycloalkyl can be replaced by O, S, OC(O), CO,                NRC or NR^(c)—CO,            -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                substituted with one to five substituents independently                selected from the group consisting of C₁₋₃₀-alkyl,                C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)R^(d), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), N[C(O)R^(c)][C(O)R^(d)], SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, CN and NO₂;                -   wherein                -   R^(c) and R^(d) are independently selected from the                    group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl                    and C₂₋₃₀-alkynyl,                -   R^(Sij), R^(Sik) and R^(Sil) are independently                    selected from the group consisting of H,                    C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered                    heteroaryl, O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl,                    O—C₂₋₃₀-alkynyl, O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl,                    O-5 to 10 membered heteroaryl,                    —[O—SiR^(Sim)R^(Sin)]_(q)—R^(Sio), NR⁷R⁸, halogen,                    and O—C(O)—R⁷,                -   wherein                -   q is an integer from 1 to 50,                -   R^(Sim), R^(Sin), R^(Sio) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, —[O—SiR^(Sip)R^(Siq)]_(r)—R^(Sir),                    NR⁷⁰R⁸⁰, halogen, and O—C(O)—R⁷⁰;                -   wherein                -   r is an integer from 1 to 50,                -   R^(Sip), R^(Siq), R^(Sir) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, O—Si(CH₃)₃, NR⁷⁰⁰R⁸⁰⁰, halogen and                    O—C(O)—R⁷⁰⁰,                -   R⁷, R⁸, R⁷⁰, R⁸⁰, R⁷⁰⁰ and R⁸⁰⁰ are independently                    selected from the group consisting of H,                    C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, and 5 to 10 membered                    heteroaryl,            -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be                substituted with one to ten substituents selected from                the group consisting of halogen, CN and NO₂,

R², R^(2′), R^(2″), R* are at each occurrence independently selectedfrom the group consisting of hydrogen, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl,C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl, 5 to 20 memberedheteroaryl, OR²¹, OC(O)—R²¹, C(O)—OR²¹, C(O)—R²¹, NR²¹R₂₂, NR²¹—C(O)R²²,C(O)—NR²¹R²², N[C(O)R²¹][C(O)R²²], SR²¹, halogen, CN,SiR^(Sis)R^(Sit)R^(Siu) and OH,

-   -   wherein    -   R²¹ and R²² and are independently selected from the group        consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,        C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl,        and    -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be substituted        with one to ten substituents independently selected from the        group consisting of C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14        membered heteroaryl, OR^(e), OC(O)—R^(e), C(O)—OR^(e),        C(O)—R^(e), NR^(e)R^(f), NR^(e)—C(O)R^(f), C(O)—NR^(e)R^(f),        N[C(O)Re][C(O)R^(f)], SR^(e), halogen, CN,        SiR^(Sis)R^(Sit)R^(Siu) and NO₂; and at least two CH₂-groups,        but not adjacent CH₂-groups, of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and        C₂₋₃₀-alkynyl can be replaced by O or S,    -   C₅₋₁₂-cycloalkyl can be substituted with one to six substituents        independently selected from the group consisting of C₁₋₂₀-alkyl,        C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5        to 14 membered heteroaryl, OR^(e), OC(O)—R^(e), C(O)—OR^(e),        C(O)—R^(e), NR^(e)R^(f), NR^(e)—C(O)R^(f), C(O)—NR^(e)R^(f),        N[C(O)R^(e)][C(O)R^(f)], SR^(e), halogen, CN,        SiR^(Sis)R^(Sit)R^(Siu) and NO₂; and one or two CH₂-groups, but        not adjacent CH₂-groups, of C₅₋₁₂-cycloalkyl can be replaced by        O, S, OC(O), CO, NR^(e) or NR^(e)—CO,    -   C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted        with one to six substituents independently selected from the        group consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,        C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,        OR^(e), OC(O)—R^(e), C(O)—OR^(e), C(O)—R^(e), NR^(e)R^(f),        NR^(e)—C(O)R^(f), C(O)—NR^(e)R^(f), N[C(O)Re][C(O)R^(f)],        SR^(e), halogen, CN, SiR^(Sis)R^(Sit)R^(Siu) and NO₂,        -   wherein        -   R^(Sis), R^(Sit) and R^(Siu) are independently from each            other selected from the group consisting of H, C₁₋₂₀-alkyl,            C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, phenyl and            O—Si(CH₃)₃,        -   R^(e) and R^(f) are independently selected from the group            consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered            heteroaryl,            -   wherein            -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5                to 10 membered heteroaryl, OR^(g), OC(O)—R^(g),                C(O)—OR^(g), C(O)—R^(g), NR^(g)R^(h), NR^(g)—C(O)R^(h),                C(O)—NR^(g)R^(h), N[C(O)R^(g)][C(O)R^(h)], SR^(g),                halogen, CN, and NO₂;        -   C₅₋₈-cycloalkyl can be substituted with one to five            substituents selected from the group consisting of            C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl,            C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(g),            OC(O)—R^(g), C(O)—OR^(g), C(O)—R^(g), NR^(g)R^(h),            NR^(g)-C(O)R^(h), C(O)—NR^(g)R^(h), N[C(O)R^(g)][C(O)R^(h)],            SR^(g), halogen, CN, and NO₂;        -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be            substituted with one to five substituents independently            selected from the group consisting of C₁₋₁₀-alkyl,            C₂₋₁₀-alkenyl, C2-10-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5            to 10 membered heteroaryl, OR^(g), OC(O)—R^(g), C(O)—OR^(g),            C(O)—R^(g), NR^(g)R^(h), NR^(g)—C(O)R^(h), C(O)—NR^(g)R^(h),            N[C(O)R^(g)][C(O)R^(h)], SR^(g), halogen, CN, and NO₂;            -   wherein            -   R^(g) and R^(h) are independently selected from the                group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and                C₂₋₁₀-alkynyl,                -   wherein                -   C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be                    substituted with one to five substituents selected                    from the group consisting of halogen, CN and NO₂,

L¹ and L² are independently from each other and at each occurrenceselected from the group consisting of C₆₋₃₀-arylene, 5 to 30 memberedheteroarylene,

wherein

C₆₋₃₀-arylene and 5 to 30 membered heteroarylene can be substituted withone to six substituents R³ at each occurrence selected from the groupconsisting of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, OR³¹,OC(O)—R³¹, C(O)—OR³¹, C(O)—R³¹, NR³¹R³², NR³¹—C(O)R³², C(O)—NR³¹R³²,N[C(O)R³¹][C(O)R³²], SR³¹, halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and OH,and

wherein

can be substituted with one or two substituents R⁴ at each occurrenceselected from the group consisting of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl,C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 memberedheteroaryl, C(O)—R⁴¹, C(O)—NR⁴¹R⁴², C(O)—OR⁴¹ and CN,

-   -   wherein    -   R³¹, R³², R⁴¹ and R⁴² are independently from each other and at        each occurrence selected from the group consisting of H,        C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl,        C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, and    -   wherein    -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be substituted        with one to ten substituents independently selected from the        group consisting of C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14        membered heteroaryl, OR^(i), OC(O)—R^(i), C(O)—OR^(i),        C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j),        N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN,        SiR^(Siv)R^(Siw)R^(Six) and NO₂; and at least two CH₂-groups,        but not adjacent CH₂-groups of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and        C₂₋₃₀-alkynyl can be replaced by O or S,    -   C₅₋₁₂-cycloalkyl can be substituted with one to six substituents        independently selected from the group consisting of C₁₋₂₀-alkyl,        C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5        to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i),        C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j),        N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN,        SiR^(Siv)R^(Siw)R^(Six) and NO₂; and one or two CH₂-groups, but        not adjacent CH₂-groups, of C₅₋₁₂-cycloalkyl can be replaced by        O, S, OC(O), CO, NR^(j) or NR^(i)—CO,    -   C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted        with one to six substituents independently selected from the        group consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,        C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,        OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j),        NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)],        SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂,        -   wherein        -   R^(Siv), R^(Siw), R^(Six) are independently from each other            selected from the group consisting of H, C₁₋₂₀-alkyl,            C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, phenyl and            O—Si(CH₃)₃,        -   R^(i) and R^(j) are independently selected from the group            consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered            heteroaryl,            -   wherein            -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5                to 10 membered heteroaryl, OR^(k), OC(O)—R^(l),                C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)-C(O)R^(l),                C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k),                halogen, CN, and NO₂;            -   C₅₋₈-cycloalkyl can be substituted with one to five                substituents selected from the group consisting of                C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,                C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered                heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k),                C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l),                C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k),                halogen, CN, and NO₂;            -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                substituted with one to five substituents independently                selected from the group consisting of C₁₋₁₀-alkyl,                C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, 5 to 10 membered heteroaryl OR^(k),                OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l),                NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l),                N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂;                -   wherein                -   R^(k) and R^(l) are independently selected from the                    group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl                    and C₂₋₁₀-alkynyl,                -   wherein                -   C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be                    substituted with one to five substituents selected                    from the group consisting of halogen, CN and NO₂.

Halogen can be F, Cl, Br and I.

X are preferably at each occurrence the same,

Q are preferably at each occurrence the same,

R² are preferably at each occurrence the same.

R* are preferably at each occurrence the same.

C₁₋₄-alkyl, C₁₋₁₀-alkyl, C₁₋₂₀-alkyl, C₁₋₃₀-alkyl, C₁₋₃₆-alkyl,C₁₋₅₀-alkyl, C₁₋₆₀-alkyl and C₁₋₁₀₀-alkyl can be branched or unbranched.Examples of C₁₋₄-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl and tert-butyl. Examples of C₁₋₁₀-alkyl areC₁₋₄-alkyl, n-pentyl, neopentyl, isopentyl, n-(1-ethyl)propyl, n-hexyl,n-heptyl, n-octyl, n-(2-ethyl)hexyl, n-nonyl and n-decyl. Examples ofC₁₋₂₀-alkyl are C₁₋₁₀-alkyl and n-undecyl, n-dodecyl, n-undecyl,n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl,n-heptadecyl, n-octadecyl, n-nonadecyl and n-icosyl (C₂₀). Examples ofC₁₋₃₀-alkyl, C₁₋₃₆-alkyl, C₁₋₅₀-alkyl, C₁₋₆₀-alkyl and C₁₋₁₀₀-alkyl areC₁₋₂₀-alkyl and n-docosyl (C₂₂), n-tetracosyl (C₂₄), n-hexacosyl (C₂₆),n-octacosyl (C₂₈) and n-triacontyl (C₃₀).

C₂₋₁₀-alkenyl, C₂₋₂₀-alkenyl, C₂₋₃₀-alkenyl, C₂₋₆₀-alkenyl andC₂₋₁₀₀-alkenyl can be branched or unbranched. Examples of C₁₋₂₀-alkenylare vinyl, propenyl, cis-2-butenyl, trans-2-butenyl, 3-butenyl,cis-2-pentenyl, trans-2-pentenyl, cis-3-pentenyl, trans-3-pentenyl,4-pentenyl, 2-methyl-3-butenyl, hexenyl, heptenyl, octenyl, nonenyl anddocenyl. Examples of C₂₋₂₀-alkenyl, C₂₋₆₀-alkenyl and C₂₋₁₀₀-alkenyl areC₂₋₁₀-alkenyl and linoleyl (C₁₈), linolenyl (C₁₈), oleyl (C₁₈), andarachidonyl (C₂₀). Examples of C₂₋₃₀-alkenyl are C₂₋₂₀-alkenyl anderucyl (C₂₂).

C₂₋₁₀-alkynyl, C₂₋₂₀-alkynyl, C₂₋₃₀-alkynyl, C₂₋₆₀-alkynyl andC₂₋₁₀₀-alkynyl can be branched or unbranched. Examples of C₂₋₁₀-alkynylare ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, pentynyl, hexynyl,heptynyl, octynyl, nonynyl and decynyl. Examples of C₂₋₂₀-alkynyl,C₂₋₃₀-alkenyl, C₂₋₆₀-alkynyl and C₂₋₁₀₀-alkynyl are undecynyl,dodecynyl, undecynyl, dodecynyl, tridecynyl, tetradecynyl, pentadecynyl,hexadecynyl, heptadecynyl, octadecynyl, nonadecynyl and icosynyl (C₂₀).

Examples of C₅₋₆-cycloalkyl are cyclopentyl and cyclohexyl. Examples ofC₅₋₈-cycloalkyl are C₅₋₆-cycloalkyl and cycloheptyl and cyclooctyl.C₅₋₁₂-cycloalkyl are C₅₋₈-cycloalkyl and cyclononyl, cyclodecyl,cycloundecyl and cyclododecyl.

Examples of C₆₋₁₀-aryl are phenyl,

Examples of C₆₋₁₄-aryl are C₆₋₁₀-aryl and

Examples of C₆₋₁₈-aryl are C₆₋₁₄-aryl and

5 to 10 membered heteroaryl are 5 to 10 membered monocyclic orpolycyclic, such as dicyclic, tricyclic or tetracyclic, ring systems,which comprise at least one heteroaromatic ring, and which may alsocomprise non-aromatic rings, which may be substituted by =O.

5 to 14 membered heteroaryl are 5 to 14 membered monocyclic orpolycyclic, such as dicyclic, tricyclic or tetracyclic, ring systems,which comprise at least one heteroaromatic ring, and which may alsocomprise non-aromatic rings, which may be substituted by =O.

5 to 20 membered heteroaryl are 5 to 20 membered monocyclic orpolycyclic, such as dicyclic, tricyclic or tetracyclic, ring systems,which comprise at least one heteroaromatic ring, and which may alsocomprise non-aromatic rings, which may be substituted by =O.

Examples of 5 to 10 membered heteroaryl are

Examples of 5 to 14 membered heteroaryl are the examples given for the 5to 10 membered heteroaryl and

Examples of 5 to 20 membered heteroaryl are the examples given for the 5to 14 membered heteroaryl and

wherein

R¹⁰⁰ and R¹⁰¹ are independently and at each occurrence selected from thegroup consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl, or R¹⁰⁰and R¹⁰¹, if attached to the same atom, together with the atom, to whichthey are attached, form a 5 to 12 membered ring system,

-   -   wherein    -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be substituted        with one to five substituents selected from the group consisting        of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,        OR^(q), OC(O)—R^(q), C(O)—OR^(q), C(O)—R^(q), NR^(q)R^(r),        NR^(q)—C(O)R^(r), C(O)—NR^(q)R^(r), N[C(O)R^(q)][C(O)R^(r)],        SR^(q), halogen, CN, and NO₂;    -   C₅₋₈-cycloalkyl can be substituted with one to five substituents        selected from the group consisting of C₁₋₁₀-alkyl,        C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to        10 membered heteroaryl, OR^(q), OC(O)—R^(q), C(O)—OR^(q),        C(O)—R^(q), NR^(q)R^(r), NR^(q)—C(O)R^(r), C(O)—NR^(q)R^(r),        N[C(O)R^(q)][C(O)R^(r)], SR^(q), halogen, CN, and NO₂;    -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be substituted        with one to five substituents independently selected from the        group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,        C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,        OR^(q), OC(O)—R^(q), C(O)—OR^(q), C(O)—R^(q), NR^(q)R^(r),        NR^(q)—C(O)R^(r), C(O)—NR^(q)R^(r), N[C(O)R^(q)][C(O)R^(r)],        SR^(q), halogen, CN, and NO₂;    -   5 to 12 membered ring system can be substituted with one to five        substituents selected from the group consisting of C₁₋₁₀-alkyl,        C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to        10 membered heteroaryl, OR^(q), OC(O)—R^(q), C(O)—OR^(q),        C(O)—R^(q), NR^(q)R^(r), NR^(q)—C(O)R^(r), C(O)—NR^(q)R^(r),        N[C(O)R^(q)][C(O)R^(r)], SR^(q), halogen, CN, and NO₂;        -   wherein        -   R^(q) and R^(r) are independently selected from the group            consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and            C₂₋₁₀-alkynyl,            -   wherein            -   C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of halogen, CN and NO₂.

C₆₋₃₀-arylene is a 6 to 30 membered monocyclic or polycyclic, such asdicyclic, tricyclic, tetracyclic, pentacyclic or hexacyclic ring system,which comprises at least one C-aromatic ring, and which may alsocomprise non-aromatic rings or heteroaromatic rings, which may besubstituted by =O.

Examples of C₆₋₃₀-arylene are

wherein

R¹ is at each occurrence selected from the group consisting of H,C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl, C₂₋₁₀₀-alkynyl, C₅₋₁₂-cycloalkyl,C₆₋₁₈-aryl, a 5 to 20 membered heteroaryl, C(O)—C₁₋₁₀₀-alkyl,C(O)—C₅₋₁₂-cycloalkyl and C(O)—OC₁₋₁₀₀-alkyl,

-   -   wherein    -   C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl can be        substituted with one to fourty substituents independently        selected from the group consisting of C₅₋₈-cycloalkyl,        C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(a), OC(O)—R^(a),        C(O)—OR^(a), C(O)—R^(a), NR^(a)R^(b), NR^(a)—C(O)R^(b),        C(O)—NR^(a)R^(b), N[C(O)R^(a)][C(O)R^(b)], SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), —O—Si(R^(Sia))(R^(Sib))(R^(Sic)),        halogen, CN, and NO₂; and at least two CH₂-groups, but not        adjacent CH₂-groups, of C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and        C₂₋₁₀₀-alkynyl can be replaced by O or S,    -   C₅₋₁₂-cycloalkyl can be substituted with one to six substituents        independently selected from the group consisting of C₁₋₆₀-alkyl,        C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to        14 membered heteroaryl, OR^(a), OC(O)—R^(a), C(O)—OR^(a),        C(O)—R^(a), NR^(a)R^(b), NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b),        N[C(O)R^(a)][C(O)R^(b)], SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, CN, and NO₂; and one        or two CH₂-groups, but not adjacent CH₂-groups, of        C₅₋₁₂-cycloalkyl can be replaced by O, S, OC(O), CO, NR^(a) or        NR^(a)—CO,    -   C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted        with one to six substituents independently selected from the        group consisting of C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,        C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,        OR^(a), OC(O)—R^(a), C(O)—OR^(a), C(O)—R^(a), NR^(a)R^(b),        NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b), N[C(O)R^(a)][C(O)R^(b)],        SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, CN, and NO₂,        -   wherein        -   R^(a) and R^(b) are independently selected from the group            consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl,        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl,            C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered            heteroaryl, O—C₁₋₆₀-alkyl, O—C₂₋₆₀-alkenyl, O—C₂₋₆₀-alkynyl,            O—C₅₋₈-cycloalkyl, O—C₆₋₁₄-aryl, O-5 to 14 membered            heteroaryl, —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif), NR⁵R⁶,            halogen and O—C(O)—R⁵,            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie), R^(Sif) are independently selected                from the group consisting of H, C₁₋₆₀-alkyl,                C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl,                C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, O—C₁₋₆₀-alkyl,                O—C₂₋₆₀-alkenyl, O—C₂₋₆₀-alkynyl, O—C₅₋₈-cycloalkyl,                O—C₆₋₁₄-aryl, O-5 to 14 membered heteroaryl,                —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii), NR⁵⁰R⁶⁰, halogen and                O—C(O)—R⁵⁰;                -   wherein                -   p is an integer from 1 to 50,                -   R^(Sig) R^(Sih), R^(Sii) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, O—Si(CH₃)₃, NR⁵⁰⁰R⁶⁰⁰, halogen and                    O—C(O)—R⁵⁰⁰,            -   R⁵, R⁶, R⁵⁰, R⁶⁰, R⁵⁰⁰ and R⁶⁰⁰ are independently                selected from the group consisting of H, C₁₋₆₀-alkyl,                C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl,                C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl,            -   C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and C₂₋₆₀-alkynyl can be                substituted with one to twenty substituents selected                from the group consisting of C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)R^(d), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), N[C(O)R^(c)][C(O)R^(d)], SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, CN, and NO₂;                and at least two CH₂-groups, but not adjacent                CH₂-groups, of C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and                C₂₋₆₀-alkynyl can be replaced by O or S,            -   C₅₋₈-cycloalkyl can be substituted with one to five                substituents selected from the group consisting of                C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c),                C(O)—OR^(c), C(O)—R^(c), NR^(c)R^(d), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), N[C(O)R^(c)][C(O)R^(d)], SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, CN, and NO₂;                and one or two CH₂-groups, but not adjacent CH₂-groups,                of C₅₋₈-cycloalkyl can be replaced by O, S, OC(O), CO,                NRC or NR^(c)—CO,            -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                substituted with one to five substituents independently                selected from the group consisting of C₁₋₃₀-alkyl,                C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)R^(d), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), N[C(O)R^(c)][C(O)R^(d)], SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, CN and NO₂;                -   wherein                -   R^(c) and R^(d) are independently selected from the                    group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl                    and C₂₋₃₀-alkynyl,                -   R^(Sij), R^(Sik) and R^(Sil) are independently                    selected from the group consisting of H,                    C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered                    heteroaryl, O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl,                    O—C₂₋₃₀-alkynyl, O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl,                    O-5 to 10 membered heteroaryl,                    —[O—SiR^(Sim)R^(Sin)]_(q)—R^(Sio), NR⁷R⁸, halogen,                    and O—C(O)—R⁷,                -   wherein                -   q is an integer from 1 to 50,                -   R^(Sim), R^(Sin), R^(Sio) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, —[O—SiR^(Sip)R^(Siq)]_(r)—R^(Sir),                    NR⁷⁰R⁸⁰, halogen, and O—C(O)—R⁷⁰;                -   wherein                -   r is an integer from 1 to 50,                -   R^(Sip), R^(Siq), R^(Sir) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, O—Si(CH₃)₃, NR⁷⁰⁰R⁸⁰⁰, halogen and                    O—C(O)—R⁷⁰⁰,            -   R⁷, R⁸, R⁷⁰, R⁸⁰, R⁷⁰⁰ and R⁸⁰⁰ are independently                selected from the group consisting of H, C₁₋₃₀-alkyl,                C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, and 5 to 10 membered heteroaryl,        -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be            substituted with one to ten substituents selected from the            group consisting of halogen, CN and NO₂,

R¹⁰² and R¹⁰³ are independently and at each occurrence selected from thegroup consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl, or R¹⁰²and R¹⁰³, if attached to the same atom, together with the atom, to whichthey are attached, form a 5 to 12 membered ring system,

-   -   wherein    -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be substituted        with one to five substituents selected from the group consisting        of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,        OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t),        NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)],        SR^(s), halogen, CN, and NO₂;    -   C₅₋₈-cycloalkyl can be substituted with one to five substituents        selected from the group consisting of C₁₋₁₀-alkyl,        C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to        10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s),        C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t),        N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂;    -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be substituted        with one to five substituents independently selected from the        group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,        C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,        OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t),        NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)],        SR^(s), halogen, CN, and NO₂;    -   5 to 12 membered ring system can be substituted with one to five        substituents selected from the group consisting of C₁₋₁₀-alkyl,        C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to        10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s),        C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t),        N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂;        -   wherein        -   R^(s) and R^(t) are independently selected from the group            consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and            C₂₋₁₀-alkynyl,            -   wherein            -   C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of halogen, CN and NO₂.

5 to 30 membered heteroarylene is a 5 to 30 membered monocyclic orpolycyclic, such as dicyclic, tricyclic, tetracyclic, pentacyclic orhexacyclic ring system, which comprises at least one heteroaromaticring, and which may also comprise aromatic rings or non-aromatic rings,which may be substituted by =O.

Examples of 5 to 30 membered heteroarylene are

wherein

R¹ is defined as above

X′ is at each occurrence selected from the group consisting of O, S, Seor Te, preferably O, S or Se, more preferably S or Se, most preferablyS;

R¹⁰⁴ and R¹⁰⁵ are independently and at each occurrence selected from thegroup consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl, or R¹⁰⁴and R¹⁰⁵, if attached to the same atom, together with the atom, to whichthey are attached, form a 5 to 12 membered ring system,

-   -   wherein    -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be substituted        with one to five substituents selected from the group consisting        of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,        OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t),        NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)],        SR^(s), halogen, CN, and NO₂;    -   C₅₋₈-cycloalkyl can be substituted with one to five substituents        selected from the group consisting of C₁₋₁₀-alkyl,        C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to        10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s),        C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t),        N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂;    -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be substituted        with one to five substituents independently selected from the        group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,        C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,        OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t),        NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)],        SR^(s), halogen, CN, and NO₂;    -   5 to 12 membered ring system can be substituted with one to five        substituents selected from the group consisting of C₁₋₁₀-alkyl,        C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to        10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s),        C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t),        N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂;        -   wherein        -   R^(s) and R^(t) are independently selected from the group            consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and            C₂₋₁₀-alkynyl,            -   wherein            -   C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of halogen, CN and NO₂.

The 5 to 12 membered ring system can contain, in addition to the atom,to which R¹⁰⁰ and R¹⁰¹, respectively R¹⁰² and R¹⁰³, respectively R¹⁰⁴and R¹⁰⁵, are attached, ring members selected from the group consistingof CH₂, O, S and NR^(u), werein R^(u) is at each occurrence selectedfrom the group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl andC₂₋₁₀-alkynyl.

Preferred are moieties of formulae 1, 1′, 2 and 2′, where M1 and M2enable an electronically conjugated link between L₁ and L₂.

Preferred are polymers comprising at least one unit of formulae

n, m, L1, L2, X, Q, R, R², R^(2′), R^(2″) are defined as above;

Y is at each occurrence selected from the group consisting of O, S, Seor Te, preferably O, S or Se, more preferably S or Se, most preferablyS;

More preferred are polymers comprising at least one unit of formula 1a,1b, 1d, 1e, or 1f, where n, m, L1, L2, X, Q, R, R², R^(2′), R^(2″) aredefined as above;

Even more preferred are polymers comprising at least one unit of formula

where n, m, L1, L2, X, Q, R, R², R^(2′), R^(2″) are defined as above;

Still more preferred are polymers comprising at least one unit offormula

where n, m, L1, L2, X, Q, R, R², R^(2′), R^(2″) are defined as above;

Most preferred are polymers comprising at least one unit of formula

where n, m, L1, L2, X, Q, R, R², R^(2′), R^(2″) are defined as above;

Preferably, the polymers of the present invention comprise at least 60%by weight of units of formulae (1) or (1′) based on the weight of thepolymer.

More preferably, the polymers of the present invention comprise at least80% by weight of units of formulae (1) or (1′) based on the weight ofthe polymer.

Most preferably, the polymers of the present invention essentiallyconsist of units of formulae (1) or (1′).

Preferably, R and R¹ are at each occurrence selected from the groupconsisting of H, C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl, C₂₋₁₀₀-alkynyl,C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl, and a 5 to 20 membered heteroaryl,

-   -   wherein    -   C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl can be        substituted with one to fourty substituents independently        selected from the group consisting of C₅₋₈-cycloalkyl,        C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(a), OC(O)—R^(a),        C(O)—OR^(a), C(O)—R^(a), NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b),        SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen and CN; and at least        two CH₂-groups, but not adjacent CH₂-groups, of C₁₋₁₀₀-alkyl,        C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl can be replaced by O or S,    -   C₅₋₁₂-cycloalkyl can be substituted with one to six substituents        independently selected from the group consisting of C₁₋₆₀-alkyl,        C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to        14 membered heteroaryl, OR^(a), OC(O)—R^(a), C(O)—OR^(a),        C(O)—R^(a), NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b), SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), —O—Si(R^(Sia))(R^(Sib))(R^(Sic)),        halogen, and CN; and one or two CH₂-groups, but not adjacent        CH₂-groups, of C₅₋₁₂-cycloalkyl can be replaced by O, S, OC(O),        CO, NR^(a) or NR^(a)—CO,    -   C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted        with one to six substituents independently selected from the        group consisting of C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,        C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,        OR^(a), OC(O)—R^(a), C(O)—OR^(a), C(O)—R^(a), NR^(a)—C(O)R^(b),        C(O)—NR^(a)R^(b), SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, and CN,        -   wherein        -   R^(a) and R^(b) are independently selected from the group            consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl,        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl,            C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered            heteroaryl, O—C₁₋₆₀-alkyl, O—C₂₋₆₀-alkenyl, O—C₂₋₆₀-alkynyl,            O—C₅₋₈-cycloalkyl, —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif),            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie) and R^(Sif) are independently selected                from the group consisting of H, C₁₋₆₀-alkyl,                C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl,                C₆₋₁₄-aryl, —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),                -   wherein                -   p is an integer from 1 to 50,                -   R^(Sig) R^(Sih) and R^(Sii) are independently                    selected from the group consisting of H,                -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, O—Si(CH₃)₃,            -   C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and C₂₋₆₀-alkynyl can be                substituted with one to twenty substituents selected                from the group consisting of C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)—C(O)R^(d), C(O)—NR^(c)R^(d), SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, and CN; and                at least two CH₂-groups, but not adjacent CH₂-groups, of                C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and C₂₋₆₀-alkynyl can be                replaced by O or S,            -   C₅₋₈-cycloalkyl can be substituted with one to five                substituents selected from the group consisting of                C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c),                C(O)—OR^(c), C(O)—R^(c), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), SR^(c), Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, and CN; and                one or two CH₂-groups, but not adjacent CH₂-groups, of                C₅₋₈-cycloalkyl can be replaced by O, S, OC(O), CO, NRC                or NR^(c)—CO,            -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                substituted with one to five substituents independently                selected from the group consisting of C₁₋₃₀-alkyl,                C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)—C(O)R^(d), C(O)—NR^(c)R^(d), SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen and CN;                -   wherein                -   R^(c) and R^(d) are independently selected from the                    group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl                    and C₂₋₃₀-alkynyl,                -   R^(Sij), R^(Sik) and R^(Sil) are independently                    selected from the group consisting of H,                    C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,                    —[O—SiR^(Sim)R^(Sin)]_(q)—R^(Sio),                -   wherein                -   q is an integer from 1 to 50,                -   R^(Sim), R^(Sin), R^(Sio) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, —[O—SiR^(Sip)R^(Siq)]_(r)—R^(Sir),                    NR⁷⁰R⁸⁰, halogen, and O—C(O)—R⁷⁰;                -   wherein                -   r is an integer from 1 to 50,                -   R^(Sip), R^(Siq), R^(Sir) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl,                    O—C₁₋₃₀-alkyl, O—C₂₋₃₀-alkenyl, O—C₂₋₃₀-alkynyl,                    O—C₅₋₆-cycloalkyl, O—C₆₋₁₀-aryl, O-5 to 10 membered                    heteroaryl, O—Si(CH₃)₃, NR⁷⁰⁰R⁸⁰⁰, halogen and                    O—C(O)—R⁷⁰⁰,                -   R⁷⁰, R⁸⁰, R⁷⁰⁰ and R⁸⁰⁰ are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, and 5 to 10 membered heteroaryl,            -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be                substituted with one to ten substituents selected from                the group consisting of halogen and CN.

More preferably, R and R¹ are at each occurrence selected from the groupconsisting of C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl,

-   -   wherein    -   C₁₋₁₀₀-alkyl, C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl can be        substituted with one to fourty substituents independently        selected from the group consisting of C₅₋₈-cycloalkyl,        C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(a), OC(O)—R^(a),        C(O)—OR^(a), C(O)—R^(a), NR^(a)—C(O)R^(b), C(O)—NR^(a)R^(b),        SR^(a), Si(R^(Sia))(R^(Sib))(R^(Sic)),        —O—Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, and CN; and at least        two CH₂-groups, but not adjacent CH₂-groups, of C₁₋₁₀₀-alkyl,        C₂₋₁₀₀-alkenyl and C₂₋₁₀₀-alkynyl can be replaced by O or S,        -   wherein        -   R^(a) and R^(b) are independently selected from the group            consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl,        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl,            C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl,            —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif),            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie) and R^(Sif) are independently selected                from the group consisting of H, C₁₋₆₀-alkyl,                C₂₋₆₀-alkenyl, C₂₋₆₀-alkynyl, C₅₋₈-cycloalkyl,                C₆₋₁₄-aryl, —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),                -   wherein                -   p is an integer from 1 to 50,                -   R^(Sig) R^(Sih), R^(Sii) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, O—Si(CH₃)₃,            -   C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and C₂₋₆₀-alkynyl can be                substituted with one to twenty substituents selected                from the group consisting of C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)—C(O)R^(d), C(O)—NR^(c)R^(d), SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, and CN; and                at least two CH₂-groups, but not adjacent CH₂-groups, of                C₁₋₆₀-alkyl, C₂₋₆₀-alkenyl and C₂₋₆₀-alkynyl can be                replaced by O or S,            -   C₅₋₈-cycloalkyl can be substituted with one to five                substituents selected from the group consisting of                C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c),                C(O)—OR^(c), C(O)—R^(c), NR^(c)—C(O)R^(d),                C(O)—NR^(c)R^(d), SR^(c), Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, and CN; and                one or two CH₂-groups, but not adjacent CH₂-groups, of                C₅₋₈-cycloalkyl can be replaced by O, S, OC(O), CO, NRC                or NR^(c)—CO,            -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                substituted with one to five substituents independently                selected from the group consisting of C₁₋₃₀-alkyl,                C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, OR^(c), OC(O)—R^(c), C(O)—OR^(c),                C(O)—R^(c), NR^(c)—C(O)R^(d), C(O)—NR^(c)R^(d), SR^(c),                Si(R^(Sij))(R^(Sik))(R^(Sil)),                —O—Si(R^(Sij))(R^(Sik))(R^(Sil)), halogen, and CN;                -   wherein                -   R^(c) and R^(d) are independently selected from the                    group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl                    and C₂₋₃₀-alkynyl,                -   R^(Sij), R^(Sik) and R^(Sil) are independently                    selected from the group consisting of H,                    C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,                    —[O—SiR^(Sim)R^(Sin)]_(q)—R^(Sio),                -   wherein                -   q is an integer from 1 to 50,                -   R^(Sim), R^(Sin), R^(Sio) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, —[O—SiR^(Sip)R^(Siq)]_(r)—R^(Sir),                -   wherein                -   r is an integer from 1 to 50,                -   R^(Sip), R^(Siq), R^(Sir) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, O—Si(CH₃)₃,            -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be                substituted with one to ten substituents selected from                the group consisting of halogen and CN.

Even more preferably, R and R¹ are at each occurrence selected from thegroup consisting of C₁₋₅₀-alkyl, C₂₋₅₀-alkenyl and C₂₋₅₀-alkynyl,

-   -   wherein    -   C₁₋₅₀-alkyl, C₂₋₅₀-alkenyl and C₂₋₃₀-alkynyl can be substituted        with one to twenty substituents independently selected from the        group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10        membered heteroaryl, OR^(a), SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), —O—Si(R^(Sia))(R^(Sib))(R^(Sic)),        halogen, and CN; and at least two CH₂-groups, but not adjacent        CH₂-groups, of C₁₋₅₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₅₀-alkynyl can        be replaced by O or S,    -   wherein    -   R^(a) is independently selected from the group consisting of H,        C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl and        C₆₋₁₀-aryl,    -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from the        group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl,        C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,        —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif),        -   wherein        -   o is an integer from 1 to 50,        -   R^(Sid), R^(Sie), R^(Sif) are independently selected from            the group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl,            C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,            —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),            -   wherein            -   p is an integer from 1 to 50,            -   R^(Sig) R^(Sih), R^(Sii) are independently selected from                the group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl,                C₂₋₃₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, O—Si(CH₃)₃,    -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be substituted        with one to ten substituents selected from the group consisting        of halogen and CN.

Still more preferably, R and R¹ are at each occurrence selected from thegroup consisting of C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl,

-   -   wherein    -   C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl can be substituted        with one to twenty substituents independently selected from the        group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10        membered heteroaryl, OR^(a), SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), halogen, and CN; and at least two        CH₂-groups, but not adjacent CH₂-groups, of C₁₋₃₆-alkyl,        C₂₋₃₆-alkenyl and C₂₋₃₆-alkynyl can be replaced by O or S,        -   wherein        -   R^(a) is independently selected from the group consisting of            H, C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl, C₃₋₂₀-alkynyl,            C₅₋₆-cycloalkyl and C₆₋₁₀-aryl        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl,            C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,            —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif)            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie), R^(Sif) are independently selected                from the group consisting of H, C₁₋₃₀-alkyl,                C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),                -   wherein                -   p is an integer from 1 to 50,            -   R^(Sig) R^(Sih), R^(Sii) are independently selected from                the group consisting of H, C₁₋₃₀-alkyl, C₂₋₂₀-alkenyl,                C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, O—Si(CH₃)₃,        -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be            substituted with one to ten substituents selected from the            group consisting of halogen and CN.

Most preferably, R and R¹ are at each occurrence selected from the groupconsisting of C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₃₀-alkynyl,

-   -   wherein    -   C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl can be substituted        with one to ten substituents independently selected from the        group consisting of OR^(a), SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), and halogen; and at least two        CH₂-groups, but not adjacent CH₂-groups, of C₁₋₅₀-alkyl,        C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl can be replaced by O or S,        -   wherein        -   R^(a) is independently selected from the group consisting of            H, C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl, C₃₋₂₀-alkynyl,            C₅₋₆-cycloalkyl and C₆₋₁₀-aryl        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl,            C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,            —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif)            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie), R^(Sif) are independently selected                from the group consisting of H, C₁₋₃₀-alkyl,                C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),                -   wherein                -   p is an integer from 1 to 50,            -   R^(Sig) R^(Sih), R^(Sii) are independently selected from                the group consisting of H, C₁₋₃₀-alkyl, C₂₋₂₀-alkenyl,                C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, O—Si(CH₃)₃,        -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be            substituted with one to ten substituents selected from the            group consisting of halogen and CN.

Especially preferably, R and R¹ are at each occurrence selected from thegroup consisting of C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl,

-   -   wherein    -   C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl can be substituted        with one to ten fluorine groups; and at least two CH₂-groups,        but not adjacent CH₂-groups, of C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and        C₃₋₅₀-alkynyl can be replaced by O or S.

In particular, R and R¹ are at each occurrence unsubstitutedC₁₋₅₀-alkyl, C₃₋₅₀-alkenyl and C₃₋₅₀-alkynyl, especially C₁₋₃₆-alkyl,more especially C₈₋₃₆-alkyl.

Preferably, R², R^(2′), R^(2″) and R* are at each occurrence selectedfrom the group consisting of hydrogen, C₁₋₃₀-alkyl, and halogen,

-   -   wherein    -   C₁₋₃₀-alkyl can be substituted with one to ten substituents        independently selected from the group consisting of        C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,        OR^(e), OC(O)—R^(e), C(O)—OR^(e), C(O)—R^(e), NR^(e)R^(f),        NR^(e)—C(O)R^(f), C(O)—NR^(e)R^(f), N[C(O)R^(e)][C(O)R^(f)],        SR^(e), halogen, CN, SiR^(Sis)R^(Sit)R^(Siu) and NO₂; and at        least two CH₂-groups, but not adjacent CH₂-groups, of        C₁₋₃₀-alkyl can be replaced by O or S,        -   wherein        -   R^(Sis), R^(Sit) and R^(Siu) are independently from each            other selected from the group consisting of H, C₁₋₂₀-alkyl,            C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, phenyl and            O—Si(CH₃)₃,        -   R^(e) and R^(f) are independently selected from the group            consisting of H, C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl, C₃₋₂₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered            heteroaryl,            -   wherein            -   C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl and C₃₋₂₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5                to 10 membered heteroaryl, OR^(g), OC(O)—R^(g),                C(O)—OR^(g), C(O)—R^(g), NR^(g)R^(h), NR^(g)—C(O)R^(h),                C(O)—NR^(g)R^(h), N[C(O)R^(g)][C(O)R^(h)], SR^(g),                halogen, CN, and NO₂;            -   C₅₋₈-cycloalkyl can be substituted with one to five                substituents selected from the group consisting of                C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,                C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered                heteroaryl, OR^(g), OC(O)—R^(g), C(O)—OR^(g),                C(O)—R^(g), NR^(g)R^(h), NR^(g)—C(O)R^(h),                C(O)—NR^(g)R^(h), N[C(O)R^(g)][C(O)R^(h)], SR^(g),                halogen, CN, and NO₂;            -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                substituted with one to five substituents independently                selected from the group consisting of C₁₋₁₀-alkyl,                C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(g),                OC(O)—R^(g), C(O)—OR^(g), C(O)—R^(g), NR^(g)R^(h),                NR^(g)—C(O)R^(h), C(O)—NR^(g)R^(h),                N[C(O)R^(g)][C(O)R^(h)], SR^(g), halogen, CN, and NO₂;            -   wherein            -   R^(g) and R^(h) are independently selected from the                group consisting of H, C₁₋₁₀-alkyl, C₃₋₁₀-alkenyl and                C₃₋₁₀-alkynyl,                -   wherein                -   C₁₋₁₀-alkyl, C₃₋₁₀-alkenyl and C₃₋₁₀-alkynyl can be                    substituted with one to five substituents selected                    from the group consisting of halogen, CN and NO₂.

More preferably, R², R^(2′), R^(2″) and R* are at each occurrenceselected from the group consisting of hydrogen, unsubstitutedC₁₋₃₀-alkyl and halogen.

In particular, R², R^(2′), R^(2″) and R* are in each occurrencehydrogen.

Preferably, n is 0, 1 or 2. More preferably, n is 0 or 1. Mostpreferably, n is 0.

Preferably, m is 0, 1 or 2.

In some embodiments, L¹ and L² are independently from each other and ateach occurrence preferably selected from the group consisting ofC₆₋₃₀-arylene, 5 to 30 membered heteroarylene,

-   -   and

-   -   wherein    -   C₆₋₃₀-arylene and 5 to 30 membered heteroarylene can be        substituted with one to six substituents R³ at each occurrence        selected from the group consisting of C₁₋₃₀-alkyl,        C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5        to 20 membered heteroaryl, OR³¹, OC(O)—R³¹, C(O)—OR³¹, C(O)—R³¹,        NR³¹R³², NR³¹—C(O)R³², C(O)—NR³¹R³², SR³¹, halogen, CN,        SiR^(Siv)R^(Siw)R^(Six) and OH, and    -   wherein

-   -   can be substituted with one or two substituents R⁴ at each        occurrence selected from the group consisting of C₁₋₃₀-alkyl,        C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5        to 20 membered heteroaryl, C(O)—R⁴¹, C(O)—NR⁴¹R⁴², C(O)—OR⁴¹ and        CN,        -   wherein        -   R³¹, R³², R⁴¹ and R⁴² are independently from each other and            at each occurrence selected from the group consisting of H,            C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl,            C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, and        -   wherein        -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be            substituted with one to ten substituents independently            selected from the group consisting of C₅₋₈-cycloalkyl,            C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i),            OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j),            NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)],            SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and at            least two CH₂-groups, but not adjacent CH₂-groups of            C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be replaced            by O or S,        -   C₅₋₁₂-cycloalkyl can be substituted with one to six            substituents independently selected from the group            consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,            OR^(i), OC(O)—R^(i), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j),            NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)],            SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and            one or two CH₂-groups, but not adjacent CH₂-groups, of            C₅₋₁₂-cycloalkyl can be replaced by O, S, OC(O), CO, NR^(i)            or NR^(i)—CO,        -   C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be            substituted with one to six substituents independently            selected from the group consisting of C₁₋₂₀-alkyl,            C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5            to 14 membered heteroaryl, OR^(i), OC(O)—R^(i), C(O)—OR^(i),            C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j),            N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN,            SiR^(Siv)R^(Siw)R^(Six) and NO₂,            -   wherein            -   R^(Siv), R^(Siw), R^(Six) are independently from each                other selected from the group consisting of H,                C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,                C₅₋₆-cycloalkyl, phenyl and O—Si(CH₃)₃,            -   R^(i) and R^(j) are independently selected from the                group consisting of H, C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl,                C₃₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14                membered heteroaryl,                -   wherein                -   C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl and C₃₋₂₀-alkynyl can be                    substituted with one to five substituents selected                    from the group consisting of C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k),                    OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l),                    NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l),                    N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and                    NO₂;                -   C₅₋₈-cycloalkyl can be substituted with one to five                    substituents selected from the group consisting of                    C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered                    heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k),                    C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l),                    C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k),                    halogen, CN, and NO₂;                -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be                    substituted with one to five substituents                    independently selected from the group consisting of                    C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl,                    C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered                    heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k),                    C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l),                    C(O)—NR^(k)R^(l), N[C(O)R^(l)][C(O)R^(l)], SR^(k),                    halogen, CN, and NO₂;                -   wherein                -   R^(k) and R^(l) are independently selected from the                    group consisting of H,                -   C₁₋₁₀-alkyl, C₃₋₁₀-alkenyl and C₃₋₁₀-alkynyl,                -   wherein                -   C₁₋₁₀-alkyl, C₃₋₁₀-alkenyl and C₃₋₁₀-alkynyl can be                    substituted with one to five substituents selected                    from the group consisting of halogen, CN and NO₂.

In some other embodiments, L¹ and L² are independently from each otherand at each occurrence selected from the group consisting ofC₆-C₃₀-arylene and 5 to 30 membered heteroarylene,

-   -   and

-   -   wherein    -   C₆₋C₃₀-arylene and 5 to 30 membered heteroarylene can be        substituted with one to six substituents R³ at each occurrence        selected from the group consisting of C₁₋₃₀-alkyl,        C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5        to 20 membered heteroaryl, OR³¹, OC(O)—R³¹, C(O)—OR³¹, C(O)—R³¹,        NR³¹R³², NR³¹—C(O)R³², C(O)—NR³¹R³², SR³¹, halogen, CN,        SiR^(Siv)R^(Siw)R^(Six) and OH, and    -   wherein

-   -   can be substituted with one or two substituents R⁴ at each        occurrence selected from the group consisting of C₁₋₃₀-alkyl,        C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5        to 20 membered heteroaryl, C(O)—R⁴¹, C(O)—NR⁴¹R⁴², C(O)—OR⁴¹ and        CN,        -   wherein        -   R³¹, R³², R⁴¹ and R⁴² are independently from each other and            at each occurrence selected from the group consisting of H,            C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl,            C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, and        -   wherein        -   C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be            substituted with one to ten substituents independently            selected from the group consisting of C₅₋₈-cycloalkyl,            C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i),            OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j),            NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)],            SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and at            least two CH₂-groups, but not adjacent CH₂-groups of            C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be replaced            by O or S,        -   C₅₋₁₂-cycloalkyl can be substituted with one to six            substituents independently selected from the group            consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl,            C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl,            OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j),            NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)],            SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and            one or two CH₂-groups, but not adjacent CH₂-groups, of            C₅₋₁₂-cycloalkyl can be replaced by O, S, OC(O), CO, NR^(i)            or NR^(i)—CO.

Preferably, L¹ and L² are independently from each other and at eachoccurrence selected from the group consisting of C₆₋₃₀-arylene and 5 to30 membered heteroarylene,

-   -   and

wherein C₆₋₃₀-arylene and 5 to 30 membered heteroarylene is selectedfrom the group consisting of

-   -   wherein    -   R¹⁰⁴ and R¹⁰⁵ are independently and at each occurrence selected        from the group consisting of H, or C₁₋₂₀-alkyl and C₆₋₁₄-aryl,        -   wherein        -   C₁₋₂₀-alkyl can be substituted with one to five substituents            selected from the group consisting of OR^(s)and halogen;        -   C₆₋₁₄-aryl can be substituted with one to five substituents            independently selected from the group consisting of            C₁₋₁₀-alkyl, OR^(s) and halogen;        -   wherein        -   R^(s) is independently selected from the group consisting of            H and C₁₋₁₀-alkyl,

R¹ is at each occurrence selected from the group consisting ofC₁₋₃₆-alkyl, C₃₋₃₆-alkenyl and C₃₋₃₆-alkynyl,

-   -   wherein    -   C₁₋₃₆-alkyl, C₃₋₃₆-alkenyl and C₃₋₃₆-alkynyl can be substituted        with one to twenty substituents independently selected from the        group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10        membered heteroaryl, OR^(a), SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), —O—Si(R^(Sia))(R^(Sib))(R^(Sic)),        halogen, and CN; and at least two CH₂-groups, but not adjacent        CH₂-groups, of C₁₋₃₆-alkyl, C₂₋₃₆-alkenyl and C₂₋₃₆-alkynyl can        be replaced by O or S,        -   wherein        -   R^(a) is independently selected from the group consisting of            H, C₁₋₂₀-alkyl, C₃₋₂₀-alkenyl, C₃₋₂₀-alkynyl,            C₅₋₆-cycloalkyl and C₆₋₁₀-aryl        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl,            C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,            —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif)            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie), R^(Sif) are independently selected                from the group consisting of H, C₁₋₃₀-alkyl,                C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),                -   wherein                -   p is an integer from 1 to 50,            -   R^(Sig) R^(Sih), R^(Sii) are independently selected from                the group consisting of H, C₁₋₃₀-alkyl, C₂₋₂₀-alkenyl,                C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, O—Si(CH₃)₃,        -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be            substituted with one to ten substituents selected from the            group consisting of halogen and CN.    -   wherein    -   C₆₋₃₀-arylene and 5 to 30 membered heteroarylene can be        substituted with one to six substituents R³ at each occurrence        selected from the group consisting of C₁₋₃₀-alkyl, C₁₋₃₀-alkoxy,        CN and halogen, and    -   wherein

-   -   can be substituted with one or two substituents R⁴ at each        occurrence selected from the group consisting of C₁₋₃₀-alkyl,        C(O)—R⁴¹, C(O)—OR⁴¹ and CN,        -   wherein        -   R⁴¹ is at each occurrence C₁₋₃₀-alkyl.

More preferably, L¹ and L² are independently from each other and at eachoccurrence C₆₋₃₀-arylene and 5 to 30 membered heteroarylene

-   -   and

wherein C₆₋₃₀-arylene and 5 to 30 membered heteroarylene is selectedfrom the group consisting of

-   -   wherein    -   R¹⁰⁴ and R¹⁰⁵ are independently and at each occurrence selected        from the group consisting of H and C₁₋₂₀-alkyl,    -   X′ is O, S, or Se, preferably S or Se, particularly preferably        S.

R¹ are independently and at each occurrence a C₁₋₃₆-alkyl group,

-   -   wherein    -   5 to 30 membered heteroarylene can be substituted with one to        six substituents R³ at each occurrence selected from the group        consisting of C₁₋₃₀-alkyl, C₁₋₃₀-alkoxy, CN and halogen,    -   wherein

-   -   is unsubtituted.

In particular, L¹ and L² are independently from each other and at eachoccurrence C₆₋₃₀-arylene and 5 to 30 membered heteroarylene

-   -   and

wherein C₆₋₃₀-arylene and 5 to 30 membered heteroarylene is selectedfrom the group consisting of

-   -   wherein    -   5 to 30 membered heteroarylene is unsubstituted,    -   X′ is O, S, or Se, preferably S or Se, particularly preferably        S.    -   R¹ are independently and at each occurrence a group C₁₋₃₆-alkyl.

In even more preferred polymers comprising at least one unit of formulae(1) or (1′)

R¹ is at each occurrence selected from the group consisting ofC₁₋₃₆-alkyl, C₂₋₃₆-alkenyl and C₂₋₃₆-alkynyl,

-   -   wherein    -   C₁₋₃₆-alkyl, C₂₋₃₆-alkenyl and C₂₋₃₆-alkynyl can be substituted        with one to twenty substituents independently selected from the        group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10        membered heteroaryl, OR^(a), SR^(a),        Si(R^(Sia))(R^(Sib))(R^(Sic)), —O—Si(R^(Sia))(R^(Sib))(R^(Sic)),        halogen, and CN; and at least two CH₂-groups, but not adjacent        CH₂-groups, of C₁₋₃₆-alkyl, C₂₋₃₆-alkenyl and C₂₋₃₆-alkynyl can        be replaced by O or S,        -   wherein        -   R^(a) and R^(b) are independently selected from the group            consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl,            C₅₋₆-cycloalkyl and C₆₋₁₀-aryl        -   R^(Sia), R^(Sib) and R^(Sic) are independently selected from            the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl,            C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl,            —[O—SiR^(Sid)R^(Sie)]_(o)—R^(Sif)            -   wherein            -   o is an integer from 1 to 50,            -   R^(Sid), R^(Sie), R^(Sif) are independently selected                from the group consisting of H, C₁₋₃₀-alkyl,                C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl,                C₆₋₁₀-aryl, —[O—SiR^(Sig)R^(Sih)]_(p)—R^(Sii),                -   wherein                -   p is an integer from 1 to 50,                -   R^(Sig) R^(Sih), R^(Sii) are independently selected                    from the group consisting of H, C₁₋₃₀-alkyl,                    C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl,                    C₆₋₁₀-aryl, O—Si(CH₃)₃,        -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be            substituted with one to ten substituents selected from the            group consisting of halogen and CN,    -   R² is at each occurrence selected from the group consisting of        unsubstituted hydrogen, C₁₋₃₀-alkyl and halogen,

n is 0 or 1,

m is 0, 1 or 2, and

L¹ and L² are independently from each other and at each occurrenceselected from the group consisting of 5 to 30 membered heteroarylene,

-   -   and

wherein 5 to 30 membered heteroarylene is selected from the groupconsisting of

-   -   wherein    -   R¹⁰⁴ and R¹⁰⁵ are independently and at each occurrence selected        from the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl,        C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered        heteroaryl, or R¹⁰⁴ and R¹⁰⁵, if attached to the same atom,        together with the atom, to which they are attached, form a 5 to        12 membered ring system,        -   wherein        -   C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be            substituted with one to five substituents selected from the            group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10            membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s),            C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t),            N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂;        -   C₅₋₈-cycloalkyl can be substituted with one to five            substituents selected from the group consisting of            C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl,            C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(s),            OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t),            NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)],            SR^(s), halogen, CN, and NO₂;        -   C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be            substituted with one to five substituents independently            selected from the group consisting of C₁₋₁₀-alkyl,            C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5            to 10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s),            C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t),            N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂;        -   5 to 12 membered ring system can be substituted with one to            five substituents selected from the group consisting of            C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl,            C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(s),            OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t),            NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)],            SR^(s), halogen, CN, and NO₂;            -   wherein            -   R^(s) and R^(t) are independently selected from the                group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and                C₂₋₁₀-alkynyl,            -   wherein            -   C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be                substituted with one to five substituents selected from                the group consisting of halogen, CN and NO₂,    -   wherein    -   5 to 30 membered heteroarylene can be substituted with one to        six substituents R³ at each occurrence selected from the group        consisting of C₁₋₃₀-alkyl and halogen, and    -   wherein

-   -   can be substituted with one or two substituents R⁴ at each        occurrence selected from the group consisting of C₁₋₃₀-alkyl,        C(O)—R⁴¹, C(O)—OR⁴¹ and CN,        -   wherein        -   R⁴¹ is at each occurrence C₁₋₃₀-alkyl.

In most preferred polymers comprising at least one unit of formulae (1)or (1′)

R¹ is at each occurrence unsubstituted C₁₋₃₆-alkyl,

R² is hydrogen,

n is 0,

m is 0, 1 or 2, and

L¹ and L² are independently from each other and at each occurrence 5 to30 membered heteroarylene,

wherein 5 to 30 membered heteroarylene is selected from the groupconsisting of

-   -   wherein    -   5 to 30 membered heteroarylene can be substituted with R³, in        particular with fluorine.

In other preferred embodiments, L₁ and L₂ are selected from

wherein

R¹ is at each occurrence unsubstituted C₁₋₃₆-alkyl,

R³ and R⁴ is hydrogen,

n is 0, 1 or 2

m is 0, 1 or 2

Particular preferred polymers of the present invention comprise at leastone unit of formula

where polymers comprising at least a group of formula 1a-1 areespecially preferred, and

wherein p is an integer from 2 to 1000

X, X′ Q, R, R², R^(2′), R^(2″) are defined as above;

In another embodiment of the present invention particularly preferredpolymers comprise at least one unit of formula

where polymers comprising at least a group of formula 1b-1 areespecially preferred, and

in still another embodiment of the present invention particularlypreferred polymers comprise at least one unit of formula

where polymers comprising at least a group of formula 1f-1 areespecially preferred, and

wherein p is an integer from 2 to 1000

X, X′ Q, R, R², R^(2′), R^(2″) are defined as above;

p is preferably 3 to 200, more preferably 4 to 100 and most preferably 5to 50,

R is preferably at each occurrence C₁₋₃₆-alkyl,

R², R^(2′) and R^(2″) are at each occurrence preferably hydrogen,

Q is preferably at each occurrence carbon,

X is preferably at each occurrence S, or Se, especially S,

X′ is preferably at each occurrence S or Se, especially S,

The polymers of the present invention have preferably a weight averagemolecular weight (M_(w)) of 1 to 10000 kDa and a number averagemolecular weight (M_(n)) of 1 to 10000 kDa. The polymers of the presentinvention have more preferably a weight average molecular weight (M_(w))of 1 to 1000 kDa and a number average molecular weight (M_(n)) of 1 to100 kDa. The polymers of the present invention have even more preferablya weight average molecular weight (M_(w)) of 5 to 1000 kDa and a numberaverage molecular weight (M_(n)) of 5 to 100 kDa. The polymers of thepresent invention have still more preferably a weight average molecularweight (M_(w)) of 10 to 1000 kDa and a number average molecular weight(M_(n)) of 10 to 100 kDa. The polymers of the present invention havemost preferably a weight average molecular weight (M_(w)) of 10 to100kDa and a number average molecular weight (M_(n)) of 5 to 60 kDa. Theweight average molecular weight (M_(w)) and the number average molecularweight (M_(n)) can be determined by gel permeation chromatography (GPC)e.g. at 80° C. using chlorobenzene or preferably at 150° C. usingtrichlorobenzene as eluent and a polystyrene as standard.

The polymers of the present invention can be prepared by methods knownin the art, e.g. by Suzuki-, Stille, Yamamoto- or directheteroaryl-polymerization.

The polymers of the present invention are preferably fully conjugatedalong the whole polymer backbone.

For examples, polymers of the present invention comprising at least oneunit of formulae (1) or (1′), wherein n is 0 and which are of formulae(1-I) or (1-I′)

wherein

p, M1, M2, Q, X, R, R², R^(2′), and L² are as defined above,

m is 0, 1, 2, 3 or 4,

can be prepared by reacting a compound of formulae (3) or (3′)

wherein Z* is at each occurrence I, Br, Cl or O—S(O)₂CF₃, and p, M1, M2,Q, X, R, R² and R^(2′) are as defined above,

with one mol equivalents of a compound of formula (10)

-   -   wherein    -   L² is as defined for the compound of formula (1-I), and

Z^(a) and Z^(b) are independently selected from the group consisting ofB(OZ¹)(OZ²), SnZ¹Z²Z³ or

-   -   wherein Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶ are independently from each        other and at each occurrence H or C₁₋₄-alkyl.

Z* is preferably at each occurrence I or Br, especially Br.

Z^(a) and Z^(b) are preferably independently selected from the groupSnZ¹Z²Z³ or

especially SnZ¹Z²Z³.

The polymer comprising a compound of formulae (1-I) or (1-I′) can alsobe obtained in analogy from compounds (4) or (4′) and (11), where themeaning of R, R², R^(2′), Q, X, L², Z*, Z^(a) and Z^(b) is definedabove:

For example, polymers of the present invention comprising at least oneunit of formulae (1) or (1′), wherein n and m are 0 and which are offormulae (1-II) or (1-II′)

wherein

p, M1, M2, Q, X, R, R², R^(2′) are as defined above,

can e.g. be prepared by reacting a compound of formulae (3) or (3′)

wherein Z* is at each occurrence I, Br, Cl or O—S(O)₂CF₃, and R, R² andR^(2′) are as defined above,

with a compound of formulae (4) or (4′)

wherein

R, R² and R^(2′) are as defined for the compound of formula (1-II), and

Z^(a) and Z^(b) are independently selected from the group consisting ofB(OZ¹)(OZ²), SnZ¹Z²Z³ or

wherein Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶ are independently from each other andat each occurrence H or C₁₋₄-alkyl.

Z* is preferably at each occurrence I or Br, especially Br.

Z^(a) and Z^(b) are preferably independently selected from the groupSnZ¹Z²Z³ or

especially SnZ¹Z²Z³.

When Z^(a) and Z^(b) are independently selected from the groupconsisting of B(OZ¹)(OZ²),

wherein Z¹, Z², z³, Z⁴, Z⁵ and Z⁶ are independently from each other andat each occurrence H or C₁₋₄-alkyl,

the reaction is usually performed in the presence of a catalyst,preferably a Pd catalyst such as Pd(P(Ph(₃)₄, Pd(OAc)₂ and Pd₂(dba)₃,and a base such as K₃PO₄, Na₂CO₃, K₂CO₃, LiOH and NaOMe. Depending onthe Pd catalyst, the reaction may also require the presence of aphosphine ligand such as P(Ph)₃, P(o-tolyl)₃and P(fe/t-Bu)₃. Thereaction is also usually performed at elevated temperatures, such as attemperatures in the range of 40 to 250° C., preferably 60 to 200° C. Thereaction can be performed in the presence of a suitable solvent such astetrahydrofuran, toluene or chlorobenzene. The reaction is usuallyperformed under inert gas.

When Z^(a) and Z^(b) are independently SnZ¹Z²Z³, wherein Z¹, Z² and Z³are independently from each other C₁₋₄-alkyl, the reaction is usuallyperformed in the presence of a catalyst, preferably a Pd catalyst suchas Pd(P(Ph(₃)₄ and Pd₂(dba)₃. Depending on the Pd catalyst, the reactionmay also require the presence of a phosphine ligand such as P(Ph)₃,P(o-tolyl)₃ and P(fe/t-Bu)₃. The reaction is also usually performed atelevated temperatures, such as at temperatures in the range of 40 to250° C., preferably 60 to 200° C. The reaction can be performed in thepresence of a suitable solvent such as toluene or chlorobenzene. Thereaction is usually performed under inert gas.

The compound of formulae (3) or (3′) can be prepared by methods known inthe art from a compound of formulae (5) or (5′).

For examples, compounds of formulae (3) or (3′), wherein

wherein Z* is I, Br, Cl or O-triflate, and R is at each occurrenceC₁₋₃₀-alkyl, R² and R^(2′) are hydrogen

can be prepared by treating a compound of formulae (5) or (5′)

wherein R is at each occurrence C₁₋₃₆-alkyl, R² and R^(2′) are hydrogenwith a Z*-donor.

Z* is preferably I or Br, especially Br.

For example, when Z* is Br, the Z*-donor can be N-bromosuccinimide. Whenusing N-bromosuccinimide as Z*-donor, the reaction can be performed at0° C. in the presence of CHCl₃/acetic acid as solvent.

A compound of formula (5) where Q is a carbon atom and M1 is a phenylring, can e.g. be prepared by the synthetic pathway, depicted inScheme 1. R², R^(2′), X and R have the meaning defined above.

R² is preferably hydrogen,

R^(2′) is preferably hydrogen,

X is preferably O, S or Se, more preferably S or Se, especially S,

R is preferably C₁₋₃₆-alkyl.

Also part of the invention are intermediates of formulae (3), (3′), (4),(4′), (5) and (5′)

wherein

R², R^(2′), R^(2″), X, Q, M1, M2, Z^(a), Z^(b) and R have the meaningdefined above.

Z* is at each occurrence I, Br, Cl or O—S(O)₂CF₃.

In preferred intermediates of formulae (3), (3′), (4), (4′), (5), (5′)at each occurrence

R² and R^(2′) are hydrogen, unsubstituted C₁₋₃₀-alkyl or halogen;

X is O, S or Se;

Q is a carbon atom;

R is hydrogen, C₁₋₃₆-alkyl, C₂₋₃₆-alkenyl, C₂₋₃₆-alkynyl,C₅₋₁₂-cycloalkyl, or phenyl, preferably C₁₋₃₆-alkyl;

Z* is at each occurrence I or Br;

Z^(a), Z^(b) are

where Z¹-Z⁴ are methyl.

In more preferred intermediates of formulae (3), (3′), (4), (4′), (5),(5′) at each occurrence

R² and R^(2′) are hydrogen or halogen;

X is S or Se;

Q is a carbon atom;

R is C₁₋₃₆-alkyl,

Z* is I or Br;

In most preferred intermediates of formulae (3), (3′), (4), (4′), (5),(5′) at each occurrence

R² and R^(2′) are hydrogen,

X is S,

is a carbon atom;

R is C₁₋₃₆-alkyl,

Z* is I or Br;

Preferred intermediates of formula (3) are

wherein

R is at each occurrence C₁₋₃₆-alkyl,

HaI is independently at each occurrence Br or I.

Particular preferred intermediates of formula (3) are

wherein, R is at each occurrence C₁₋₃₆-alkyl and R² is hydrogen.

Preferred intermediates of formula (4) are

wherein

R is at each occurrence C₁₋₃₆-alkyl.

Particular preferred intermediates of formula (4) are

wherein, R is at each occurrence C₁₋₃₆-alkyl and R² is hydrogen.

Preferred intermediates of formula (5) are

wherein

R is at each occurrence C₁₋₃₆-alkyl.

Particular preferred intermediates of formula (5) are

wherein, R is at each occurrence C₁₋₃₆-alkyl and R² is hydrogen.

In another embodiment of the present invention intermediates of formula(6) are preferred

wherein

R is at each occurrence C₁₋₃₆-alkyl

Z¹, Z² and Z³ are independently from each other C₁₋₄-alkyl.

Particular preferred intermediates of formula (6) are

Also part of the invention is an electronic device comprising thepolymer of the present invention.

The electronic device can be an organic photovoltaic device (OPVs), anorganic field-effect transistor (OFETs), an organic light emitting diode(OLEDs) or an organic photodiode (OPDs).

Preferably, the electronic device is an organic photovoltaic device(OPVs), an organic field-effect transistor (OFETs) or an organicphotodiode (OPDs).

More preferably, the electronic device is an organic field effecttransistor (OFET).

Usually, an organic field effect transistor comprises a dielectriclayer, a semiconducting layer and a substrate. In addition, an organicfield effect transistor usually comprises a gate electrode andsource/drain electrodes.

Preferably, the semiconducting layer comprises the polymer of thepresent invention. The semi-conducting layer can have a thickness of 5to 500 nm, preferably of 10 to 100 nm, more preferably of 20 to 50 nm.

The dielectric layer comprises a dielectric material. The dielectricmaterial can be silicon dioxide or aluminium oxide, or, an organicpolymer such as polystyrene (PS), poly(methylmethacrylate) (PMMA),poly(4-vinylphenol) (PVP), polyvinyl alcohol) (PVA), benzocyclobutene(BCB), or polyimide (PI). The dielectric layer can have a thickness of10 to 2000 nm, preferably of 50 to 1000nm, more preferably of 100 to 800nm.

The dielectric layer can in addition to the dielectric material comprisea self-assembled mono-layer of organic silane derivates or organicphosphoric acid derivatives. An example of an organic silane derivativeis octyltrichlorosilane. An examples of an organic phosphoric acidderivative is octyldecylphosphoric acid. The self-assembled monolayercomprised in the dielectric layer is usually in contact with thesemiconducting layer.

The source/drain electrodes can be made from any suitable organic orinorganic source/drain material. Examples of inorganic source/drainmaterials are gold (Au), silver (Ag) or copper (Cu), as well as alloyscomprising at least one of these metals. The source/drain electrodes canhave a thickness of 1 to 100 nm, preferably from 20 to 70 nm.

The gate electrode can be made from any suitable gate material such ashighly doped silicon, aluminium (Al), tungsten (W), indium tin oxide orgold (Au), or alloys comprising at least one of these metals. The gateelectrode can have a thickness of 1 to 200 nm, preferably from 5 to 100nm.

The substrate can be any suitable substrate such as glass, or a plasticsubstrate such as polyethersulfone, polycarbonate, polysulfone,polyethylene terephthalate (PET) and polyethylene naphthalate (PEN).Depending on the design of the organic field effect transistor, the gateelectrode, for example highly doped silicon can also function assubstrate.

The organic field effect transistor can be prepared by methods known inthe art.

For example, a bottom-gate top-contact organic field effect transistorcan be prepared as follows: The dielectric material, for example Al₂O₃or silicon dioxide, can be applied as a layer on a gate electrode suchas highly doped silicon wafer, which also functions as substrate, by asuitable deposition method such as atom layer deposition or thermalevaporation. A self-assembled monolayer of an organic phosphoric acidderivative or an organic silane derivative can be applied to the layerof the dielectric material. For example, the organic phosphoric acidderivative or the organic silane derivative can be applied from solutionusing solution-deposition techniques. The semiconducting layer can beformed by either solution deposition or thermal evaporation in vacuo ofthe polymer of the present invention on the self-assembled monolayer ofthe organic phosphoric acid derivative or the organic silane derivative.Source/drain electrodes can be formed by deposition of a suitablesource/drain material, for example tantalum (Ta) and/or gold (Au), onthe semiconducting layer through a shadow masks. The channel width (W)is typically 10 to 1000 μm and the channel length (L) is typically 5 to500 μm.

For example, a top-gate bottom-contact organic field effect transistorcan be prepared as follows: Sorce/drain electrodes can be formed byevaporating a suitable source/drain material, for example gold (Au), onphoto-lithographically defined electrodes on a suitable substrate, forexample a glass substrate. The semiconducting layer can be formed bydepositing a solution of the polymers of the present invention, forexample by spin-coating, on the source/drain electrodes, followed byannealing the layer at elevated temperatures such as at a temperature inthe range of 80 to 360° C. After quenching the semiconducting layer, adielectric layer can be formed by applying, for example, byspin-coating, a solution of a suitable dielectric material such aspoly(methylmethacryate), on the semiconducting layer. The gate electrodeof a suitable gate material, for example gold (Au), can be evaporatedthrough a shadow mask on the dielectric layer.

Also part of the invention is the use of the polymer of the presentinvention as semiconducting material.

The polymers of the present invention show high charge carriermobilities. In addition, the polymers of the present invention show ahigh stability, in particular a high thermal stability. Furthermore thepolymers of the present invention are compatible with liquid processingtechniques.

Also part of the invention is the use of the polymer of the presentinvention as luminescent material.

Also part of the invention is the use of the compound of the presentinvention as luminescent material.

EXAMPLES

General Experimental Details for Synthetic Part

Methods and materials: All reagents from commercial sources were usedwithout further purification. Solvents were dried and purified usingstandard techniques. Most of the compounds were characterized by NMR,usually at room temperature. High-resolution mass spectrometry (HRMS)data was recorded using a Thermo Scientific—LTQ Velos Orbitrap MS inpositive atmospheric pressure photoionization (+APPI) mode. UV-Visspectra were recorded in a Varian Cary 100 spectrophotometer.Thermogravimetric analysis (TGA) was performed under N₂ using BrukerTGA-IR TG209F1 with a ramp of 10° C./min. Differential ScanningCalorimetry (DSC) was run on DSC-204F1-phoenix. Number average (M_(n))and weight-average (M_(w)) molecular weight were determined by AgilentTechnologies 1200 series GPC running in chlorobenzene at 80° C., usingtwo PL mixed B columns in series and/or in trichlorobenzene at 150° C.and calibrated against narrow polydispersity polystyrene standards.Flash chromatography (FC) was performed on silica gel. Microwaveexperiments were performed in a Biotage initiator V 2.3.

Synthetic Details and Characterization

Example 1 Synthesis of1-bromo-2-chloro-4-(dibromomethyl)-5-fluorobenzene (J-2)

1-bromo-2-chloro-5-fluoro-4-methylbenzene (20.0 g, 90 mmol), NBS (48.06g, 270 mmol) and BPO (2.18 g, 9 mmol) dissolved in 1,2-dichloroethane(250 ml). Stirred at reflux until the starting material was consumedmonitored by GC-MS and quenched with water and extracted with ethylacetate. Organic phases collected and dried over magnesium sulfate,filtered and concentrated under vacuum. Purified via columnchromatography on silica gel with 1:1 ethyl acetate:hexane as eluent toafford a brown oil. Yield: 32.50 g (95%)

¹H NMR (700 MHz, CDCl₃) δ 7.91 (d, J=7.1 Hz, 1H), 7.36 (d, J=9.1 Hz,1H), 6.80 (s, 1H).

Example 2 Synthesis of 4-bromo-5-chloro-2-fluorobenzaldehyde (J-3)

1-bromo-2-chloro-4-(dibromomethyl)-5-fluorobenzene (34.0 g, 89.2 mmol),dissolved in formic acid (500 ml) and stirred at relfux overnight.Allowed to cool to room temperature and poured into water. The resultingsolid was collected, washed with water until the washings were no longeracidic and dried to afford a white solid. Yield: 15.32 g (72%)

¹H NMR (700 MHz, CDCl₃) δ 10.25 (s, 1H), 7.92 (d, J=6.5 Hz, 1H), 7.53(d, J=9.2 Hz, 1H).

Example 3 Synthesis of Ethyl6-bromo-5-chlorobenzo[b]thiophene-2-carboxylate (J-4)

4-bromo-5-chloro-2-fluorobenzaldehyde (22.40 g, 94.4 mmol) was dissolvedin DMSO (200 ml). Triethylamine (39.5 ml, 283.2 mmol) and ethylthioglycolate (12.4 ml, 113.2 mmol) were added and the mixture stirredat 80° C. The reaction was quenched with water when the startingmaterial was totally disapeared monitored by GC-MS and extracted withethyl acetate. The organic phases were collected, dried over magnesiumsulfate, filtered and concentrated under vacuum. The product waspurified by column chromatography on silica gel with 5:1hexane:dichloromethane as eluent. R^(e)sulting in a yellowish solid.Yield: 24.74 g (82%)

¹H NMR (400 MHz, CDCl₃) δ 8.14 (s, 1 H), 7.96 (s, 1 H), 7.94 (s, 1 H),4.43 (q, 2 H), 1.44 (t, 3H).

Example 4 Synthesis of Diethyl6,6′-(2,5-dimethyl-1,4-phenylene)bis(5-chlorobenzo[b]thiophene-2-carboxylate)(J-5)

Ethyl 6-bromo-5-chlorobenzo[b]thiophene-2-carboxylate (2 g, 6.29 mmol),2,2′-(2,5-dimethyl-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(0.90 g, 2.52 mmol) was dissolved in toluene/H₂ O (15 mL/3 mL) in a 50mL flask and digassed with argon, then Pd₂(dba)₃ (0.09 g, 0.25 mmol),(o-tol)₃ P (0.09 g, 0.76 mmol), K₃PO₄ (8.01 g, 37.74 mmol) and 2 dropsof aliquat were added into the misture and digassed with argon again.The mixture was subjected to reflux for 24 h. After cooling to roomtemperature, the reaction mixture was extracted with chloroform, and theorganic phase was collected and then passed through a short silicon gelcolumn quickly and then recrystalized from chloroform/methanol,resulting in a white solid. Yield: 1.06 g (72%)

¹H NMR (500 MHz, CDCl₃) δ 8.05 (s, 2H), 8.01 (d, J=1.9 Hz, 2H), 7.86 and7.77 (2 s (rotamers), 2H), 7.12 (s, 2H), 4.45 (q, 4H), 2.15 (s, 6H),1.45 (t, J=7.2 Hz, 6H).

Example 5 Synthesis of6,6′-(2,5-dimethyl-1,4-phenylene)bis(5-chlorobenzo[b]thiophene-2-carboxylicacid) (J-6)

Diethyl6,6′-(2,5-dimethyl-1,4-phenylene)bis(5-chlorobenzo[b]thiophene-2-carboxylate)(10 g, 17.14 mmol) was dissolved in hot ethanol (300 mL) and potassiumhydroxide (9.62 g, 171.4 mmol) in water (80 mL) added. The suspensionwas heated at reflux overnight. After cooling slightly, 6 N HCl (60 mL)was added portionwise. The residual solid was filtered, washed withwater and dried to give an off-white solid. Yield: 9.04 g (98%)

¹H NMR (700 MHz, DMSO) δ 13.68 (s, 2H), 8.25 (d, J=1.9 Hz, 2H), 8.13 (d,J=2.1 Hz, 2H), 8.11 and 8.07 (2 s (rotamers), 2H), 2.06 (s, 6H).

Example 6 Synthesis of6,6′-(2,5-dimethyl-1,4-phenylene)bis(5-chlorobenzo[b]thiophene) (J-7)

6,6′-(2,5-dimethyl-1,4-phenylene)bis(5-chlorobenzo[b]thiophene-2-carboxylicacid) (8 g, 15.21 mmol) and copper powder (2.24 g, 35 mmol) weresuspended in quinoline (120 mL) and heated at 185° C. overnight. Aftercooling down to rt, the mixture was filtered and the solid was washedwith chlorofrom and the combined organic solutions was washed with 2 NHCl twice. The residue was purified by chromatography on silica withchlorofrom/hexane to afford a white solid. Yield: 5.53 g (83%)

¹H NMR (700 MHz, DMSO, 80° C.)) δ 8.10 (s, 2H), 8.02 and 7.98 (2 s(rotamers), 2H), 7.85 (d, J=5.3 Hz, 2H), 7.48 (d, J=5.3 Hz, 2H), 7.13(s, 2H), 2.07 (s, 6H).

Example 7 Synthesis of (J-8)

A mixture of6,6′-(2,5-dimethyl-1,4-phenylene)bis(5-chlorobenzo[b]thiophene) (1 g,2.28 mmol), Pd(OAc)₂ (0.15 g, 0.228 mmol), IPr·HCl (0.19 g, 0.456 mmol),K₂CO₃ (1.26 g, 9.12 mmol) and NMP (25 mL) in a 50 mL flask was purgedwith nitrogen for 5 min. The mixture was then kept in an oil bath at170° C. overnight. After cooling to room temperature, the solution wasextracted with chloroform and washed with water. The solvents of theorganic phase were removed under reduced pressure. The residue wassubjected to chromatography on silica gel, eluting withhexane/chloroform to afford a white solid. Yield: 0.69 g (83%)

¹H NMR (700 MHz, DMSO) δ 8.51 (s, 2H), 8.15 (s, 2H), 8.05 (s, 2H), 7.70(d, J=5.3 Hz, 2H), 7.46 (d, J=5.3 Hz, 2H), 4.10 (s, 4H).

Example 8 Synthesis of Compound (J-9)

To a suspension of compound 8 (1 g, 2.73 mmol) in anhydrous DMSO (50 ml)was added sodium tert-butoxide (2.63 g, 27.3 mmol) in parts. Thereaction mixture was heated at 80° C. for 1 h, followed by the additionof 1-bromohexadecane (5 g, 16.38 mmol) dropwise. After completeaddition, the resultant mixture was heated at 85° C. for 12 h. Aftercooling to room temperature, water was added to quench the reaction,then the solution was extracted with dichloromethane and washed withwater. The solvents of the organic phase were removed under reducedpressure. The residue was subjected to chromatography on silica gel,eluting with hexane to afford a light-yellow solid. Yield: 3.45 g (81%)

¹H NMR (700 MHz, CD₂Cl₂) δ 8.24 (s, 2H), 7.79 (s, 2H), 7.75 (s, 2H),7.46 (d, J=5.3 Hz, 2H), 7.39 (d, J=5.3 Hz, 2H), 2.13-2.11 (m, 8H),0.96-1.36 (m, 104H), 0.90-0.86 (m, 12H), 0.83-0.69 (m, 8H).

Example 9 Synthesis of Compound (J-10)

To a suspension of compound 8 (1 g, 2.73 mmol) in anhydrous DMSO (50 ml)was added sodium tert-butoxide (2.63 g, 27.3 mmol) in parts. Thereaction mixture was heated at 80° C. for 1 h, followed by the additionof 2-Ethylhexyl bromide (3.16 g, 16.38 mmol) dropwise. After completeaddition, the resultant mixture was heated at 85° C. for 12 h. Aftercooling to room temperature, water was added to quench the reaction,then the solution was extracted with dichloromethane and washed withwater. The solvents of the organic phase were removed under reducedpressure. The residue was subjected to chromatography on silica gel,eluting with hexane to afford a light-yellow solid. Yield: 2.23 g (71%)

¹H NMR (700 MHz, CD₂Cl₂) δ 8.20 (s, 2H), 7.78-7.75 (m, 2H), 7.74 (d,J=3.1 Hz, 2H), 7.41 (d, J=5.3 Hz, 2H), 7.36-7.33 (d, 2H), 2.18-1.95 (m,8H), 1.02-0.41 (m, 60H).

The used di-bromo-co-monomers are commercially available

Example 10 Synthesis of Intermediate (J-11)

To a suspension of compound J-9 (1 g, 0.79 mmol) in anhydrous THF (30ml) and cooled to −78° C., then nBuLi (2.73 mmol) was added dropwisely.The reaction mixture was stirred at −78° C. for 1 h, then thetemperature was rised to room temperature and cooled again to −10° C.followed by the addition of Me₃SnCl (2.73 mmol) dropwise. After completeaddition, the resultant mixture was slowly warmed up to rt and stirredovernight. Water was added to quench the reaction, then the solution wasextracted with ethyl acetate and concentrated. The mixture was subjectedto chromatography on Al₂O₃, eluting with hexane to afford J-11 as alight-yellow oil. Yield: 1.09 g (87%)

¹H NMR (500 MHz, CD₂Cl₂) δ 8.23 (s, 2H), 7.76 (s, 2H), 7.73 (s, 2H),7.45 (s, 2H), 2.13-2.11 (m, 8H), 0.96-1.36 (m, 104H), 0.90-0.86 (m,12H), 0.83-0.69 (m, 8H), 0.44 (t, 18H).

Example 11 Synthesis of Intermediate (J-12)

To a suspension of compound J-10 (0.64 g, 0.79 mmol) in anhydrous THF(30 ml) and cooled to −78° C., then nBuLi (2.73 mmol) was addeddropwisely. The reaction mixture was stirred at −78° C. for 1 h, thenthe temperature was rised to room temperature and cooled again to −10°C. followed by the addition of Me₃SnCl (2.73 mmol) dropwise. Aftercomplete addition, the resultant mixture was slowly warmed up to rt andstirred overnight. Water was added to quench the reaction, then thesolution was extracted with ethyl acetate and concentrated. The mixturewas subjected to chromatography on Al₂O₃, eluting with hexane to afforda light-yellow solid. Yield: 0.77 g (85%)

¹H NMR (500 MHz, CD₂Cl₂) δ 8.24 (s, 2H), 7.77 (s, 2H), 7.75 (s, 2H),7.48 (s, 2H), 2.13-1.36 (m, 8H), 0.90-0.69 (m, 60H), 0.44 (t, 18H).

Examples 12-19 Synthesis of Polymers P-1 to P-8

A 2.5 mL microwave vial was charged with bis(trimethylstannyl) monomerJ-10 or J-12 (0.233 mmol), 1 eq. of dibrominated monomer (corresponding(fluorinated)benzothiadiazole or thienothiophene), 2 mol % oftris(dibenzylideneacetone)dipalladium(0) and 8 mol % of tri(o-tolyl)phosphine. The vial was sealed and chlorobenzene (1 mL) was added. Theobtained solution was degassed with argon during 30 minutes. The vialwas subjected to the following reaction conditions in the microwavereactor: 2 minutes at 100° C., 2 minutes at 120° C., 5 minutes at 140°C., 5 minutes at 160° C. and 40 minutes at 180° C. The polymer wasend-capped by addition of 0.1 eq. of 2-bromothiophene before thereaction mixture was resubmitted to the microwave reactor, 1 minute at100° C., 1 minute at 120° C., 2 minutes at 140° C. and 5 minutes at 160°C. The polymeric solution was cooled down and 0.1 eq. of2-(trimethylstannyl)thiophene was added by syringe. The reaction vialwas subjected to the previously mentioned temperature scheme to finalizethe end-capping reaction. After reaction, the crude polymer wasprecipitated in methanol and then further purified by Soxhletextractions with acetone, hexane and chloroform during 24 hours each.R^(e)maining palladium residues were removed by treating a polymericchloroform solution with an aqueous sodium diethyldithiocarbamatesolution for 2 hours at 50° C. under vigorous stirring. Afterwards theorganic phase was separated from the aqueous phase and washed severaltimes with water. The polymeric solution was concentrated under reducedpressure and precipitated into cold methanol. The polymer was filteredoff and dried under high vacuum for at least 24 hours.

Polymer P-1: ¹H NMR (500 MHz, CDCl₃) δ 8.73 (br, 2H), 8.27 (br, 2H),8.03 (br, 2H), 7.88 (br, 2H), 7.76 (br, 2H), 2.13-2.11 (br, 8H),0.96-1.36 (br, 104H), 0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H);

Polymer P-2: ¹H NMR (500 MHz, CDCl₃) δ 8.77 (br, 2H), 8.71 (br, 2H),8.28 (br, 3H), 7.90 (br, 2H), 7.77 (br, 2H), 2.13-2.11 (br, 8H),0.96-1.36 (br, 104H), 0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H);

Polymer P-3: ¹H NMR (500 MHz, CDCl₃) δ 8.75 (br, 2H), 8.32 (br, 2H),7.93 (br, 2H), 7.79 (br, 2H), 2.13-2.11 (br, 8H), 0.96-1.36 (br, 104H),0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H);

Polymer P-4: ¹H NMR (500 MHz, CDCl₃) δ 8.14 (br, 2H), 7.69 (br, 4H),7.49 (br, 2H), 7.46 (br, 2H), 2.13-2.11 (br, 8H), 0.96-1.36 (br, 104H),0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H);

Polymer P-5: ¹H NMR (500 MHz, CDCl₃) δ 8.74 (br, 2H), 8.27 (br, 2H),8.02 (br, 2H), 7.86 (br, 2H), 7.74 (br, 2H), 2.13-2.11 (br, 8H),0.96-1.36 (br, 104H), 0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H), 0.44-0.48(br, 18H);

Polymer P-6: ¹H NMR (500 MHz, CDCl₃) δ 8.76 (br, 2H), 8.73 (br, 2H),8.25 (br, 3H), 7.93 (br, 2H), 7.77 (br, 2H), 2.13-2.11 (br, 8H),0.96-1.36 (br, 104H), 0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H), 0.44-0.48(br, 18H);

Polymer P-7: ¹H NMR (500 MHz, CDCl₃) δ 8.75 (br, 2H), 8.34 (br, 2H),7.92 (br, 2H), 7.79 (br, 2H), 2.13-2.11 (br, 8H), 0.96-1.36 (br, 104H),0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H), 0.44-0.48 (br, 18H);

Polymer P-8: ¹H NMR (500 MHz, CDCl₃) δ 7.95 (br, 2H), 7.83 (br, 2H),7.71 (br, 2H), 7.40 (br, 2H), 7.23 (br, 2H), 2.13-2.11 (br, 8H),0.96-1.36 (br, 104H), 0.90-0.86 (br, 12H), 0.83-0.69 (br, 8H), 0.44-0.48(br, 18H).

GPC data:

Mn Mw Polymer KDa KDa PDI P-1 41.6 56.6 1.36 P-2 55.2 82.7 1.50 P-3 49.074.2 1.51 P-4 29.8 60.9 2.04 P-5 169.5 327.0 1.93 P-6 60.0 129.1 2.15P-7 59.3 140.9 2.37 P-8 69.5 181.6 2.61

Example 20 Synthesis of Intermediate (J-13)

Intermediate J-13 can be obtained commercially [1197732-41-4] or byliterature described methods from 1,4-dibromo-2,3-dimethyl-benzene[75024-22-5].

Example 21 Synthesis of Intermediate (J-14)

56.3 mmol (18.0 g) of compound J-4, 28.15 mmol (9.604 g) of compoundJ-13, 0.67 mmol (0.633 g) tris-(dibenzylideneacetone)-dipalladium(0)[51364-51-3] and 1.61 mmol (0.481 g) tritertbutyl-phosphonium-tetrafluoroborate [131274-22-1] were added to a 250 ml3-necked-flask equipped with a thermometer, reflux condenser with argoninlet and a septum. The system was evacuated and refilled with argon twotimes. Then 150 ml of dry and degassed tetrahydrofuran was added to thereaction flask. After dissolution of the starting material at 50° C., adegassed solution of 83 mmol (18 g) potassium phosphate in 3.8 ml ofwater was added and the reaction mixture was heated to reflux andstirred for 4 hours. The reaction mixture was allowed to cool to rt overnight, where the product precipitated. The reaction mixture wasfiltered, washed with THF and then with water and then dried to give thecrude J-14 which was used directly in the next step.

¹H NMR (400 MHz, CDCl₃) δ 8.06 (s, 2H), 8.02 (s, 2H), 7.86 and 7.79 (2 s(rotamers), 2H), 7.13 (s, 2H), 4.45 (q, 4H), 2.13 (s, 6H), 1.46 (t, 6H).

Example 22 Synthesis of Intermediate (J-15)

20 mmol (11.5 g) of compound J-14 was suspended in 300 ml of ethanol,and then a solution of 5.5 g of KOH in 20 ml of water was added to thesuspension. The suspension was then refluxed over night. The suspensionwas cooled to rt and then poured into 4 M HCl. The precipitate wasfiltered and washed well with water and then dried to give crude J-15which was used directly in the next step.

¹H NMR (400 MHz, DMSO-D₆) δ 8.28 (s, 2H), 8.15 (s, 2H), 8.10 and 8.06 (2s (rotamers), 2H), 7.13 (s, 2H), 2.06 (s, 6H).

Example 23 Synthesis of Intermediate (J-16)

11.82 mmol (6.400 g) of compound J-15 was suspended in 25 ml ofquinoline. Then 1.728 g of copper powder was added and the reactionmixture was heated for 8 hours at 185° C. The copper was allowed tosettle to the bottom of the flask, and the solution was decanted and theproduct precipitated with ethanol to give crude J-16 which was useddirectly in the next step.

¹H NMR (400 MHz, DMSO-D₆) δ 8.14 (s, 2H), 8.05 and 8.01 (2 s (rotamers),2H), 7.90 (d, 2H), 7.51 (d, 2H), 7.11 (s, 2H), 2.06 (s, 6H).

Example 24 Synthesis of Intermediate (J-17)

7.282 mmol (3.20 g) of compound J-16, 29.129 mmol (4.066 g) potassiumcarbonate, 0.728 mmol (0.163 g) palladium(II)acetate and 1.456 mmol(0.619 g) 1,3-Bis(2,6-diisopropylphenyl)imidazoliumchloride[250285-32-6] have been loaded to a 50 ml 3-necked-flask equipped with athermometer, reflux condenser with argon inlet and a septum. Then 20 mlof anhydrous N-methylpyrrolidone were added under nitrogen and thereaction mixture was stirred for 7 hours at 170° C. Then the mixture wascooled to rt and water was added. The precipitate was filtered andwashed with water and then dried to give crude J-17, which was useddirectly in the next step. The product was too insoluble to measure anNMR.

Example 25 Synthesis of Intermediate (J-18)

3.82 mmol (1.46 g) of compound J-17 were suspended in 20 ml of drydimethylsulfoxide. Then 38 mmol (3.67 g) of sodium tert-butoxide wereadded under nitrogen. The reaction mixture was heated to 85° C. for 1hour. Then a solution of 23 mmol (8.075 g) 1-iodohexadecane in 5 ml ofdimethylsulfoxide was added over a period of 2 hours. The reactionmixture was stirred over night at 85° C. The mixture was cooled to rtand water was added. The mixture was then extracted with heptane. Theheptane solution was washed with water and dried over MgSO₄ and then thesolvent was evaporated. The product was purified by columnchromatography on silica gel. Then the product was recrystallized fromethyl acetate to get compound J-18.

¹H NMR (400 MHz, CDCl₃) δ 8.18 (s, 2H), 7.85 (s, 2H), 7.69 (s, 2H), 7.44(d, 2H), 7.39 (d, 2H), 2.46 (brt, 4H), 2.10 (brt, 4H), 1.35-1.02 (m,104H), 0.90 (t, 12H), 0.62-0.58 (br, 8H).

Example 26 Synthesis of Intermediate (J-19)

0.791 mmol (1.0 g) of compound J-18 were added to a 100 ml3-necked-flask equipped with a thermometer, reflux condenser with argoninlet and a septum. The system was evacuated and refilled with argon twotimes. Then 50 ml of dry and degassed tetrahydrofuran was added to thereaction flask. After dissolution of the starting material, thetemperature was lowered to −78° C. Then 2.689 mmol (0.996 ml) of 2.7Mn-butyllithium solution in heptane were added slowly via a syringe.After stirring for 15 minutes, the reaction mixture was allowed to cometo room temperature for 1 hour. Then the temperature was reduced to −20°C. and 2.689 mmol (2.689 ml) of 1M trimethyltinchloride solution in (inhexanes) were added via a syringe. The reaction mixture was stirred thenovernight at room temperature. The reaction was quenched by the additionof water and the product was extracted with ethylacetate. The organicphase was dried over MgSO₄ and evaporated. The residue wasrecrystallized from ethyl actetate and then from heptane to yield 400 mgof compound J-19.

¹H NMR (400 MHz, CD₂Cl₂) δ 8.21 (s, 2H), 7.88 (s, 2H), 7.73 (s, 2H),7.50 (s, 2H), 2.50 (br t, 4H), 2.13 (brt, 4H), 1.35-1.04 (m, 104H), 0.90(t, 12H), 0.64-0.55 (br, 8H), 0.49 (t, 18H).

Example 27 Synthesis of Polymer (P-9)

0.019 mmol (30.2 mg) of compound J-19 and 0.019 mmol (5.6 mg) of4,7-dibromo-benzo[c]-1,2,5-thiadiazole [15155-41-6], 0.001 mmol (0.9 mg)of tris-(dibenzylideneacetone)-dipalladium(0) [51364-51-3] and 0.004mmol (1.2 mg) of tri-(o-tolyl)-phosphine [6163-58-2] were charged to a10 ml 3-necked-flask equipped with a thermometer, reflux condenser withargon inlet and a septum. The system was evacuated and refilled withargon for five times. Via a syringe 2 ml of degassed chlorobenzene wasadded. The reaction mixture was then brought to reflux for 22 hours. Thereaction mixture turned to intense red color. The reaction mixture wasadded to 20 ml of acetone, where the polymer precipitated. The polymerwas filtered and the residue washed with acetone. The polymer was takenup into toluene and refluxed for 3 hours with an aquous solution ofsodium-diethyl-dithiocarbamate to remove Pd residues. The solution wascooled to rt, separated the phases and the organic phase was washedtwice with deionized water. The toluene phase was added to aceton toprecipitate the polymer once again. After filtration, the polymer wasadded to a soxhlet thimble and extracted first with acetone, thenhexanes, and finally with toluene. The aceton fraction contained nopolymer. The hexanes and toluene fractions were added to aceton, wherethe polymer precipitated. The hexane fraction yielded 22 mg of thepolymer P-9 (GPC data (trichlorobenzene, 150° C.): Mw 32′665 PDI 2.21),and the toluene fraction yielded 7 mg of the polymer P-9.

Example 28 Synthesis of Intermediate (J-20)

64 mmol (10.0 g) of 2,6-dimethylnaphthalene were dissolved in 100 mldichloromethane and 20 mg of iodine were added. 139 mmol (22.21 g)bromine were added dropwise over 7 hours at 21° C. The mixture was thenstirred over night at rt. The organic phase was washed with aquoussodiumthiosulphate and water, dried and evaporated. The crude productwas recrystallized from ethanol to give compound J-20.

¹H NMR (400 MHz, CDCl₃) δ 8.22 (d, 2H), 7.44 (d, 2H), 2.65 (s, 6H).

Example 29 Synthesis of Intermediate (J-21)

33.4 mmol (10.50 g) of compound J-20, 94.5 mmol (24.00 g)bis(pinacolato)diborone [73183-34-3], 268 mmol (26.52 g) potassiumactetate and 2.006 mmol (1.47 g) Pd(dppf)Cl₂ [72287-26-4]were placed ina 250 ml 3-necked-flask equipped with a thermometer, reflux condenserwith argon inlet and a septum. The system was evacuated and refilledwith argon for five times. Via a syringe 80 ml of degasseddimethylformamide was added. The reaction mixture was then heated andstirred at 110° C. for 48 hours. The mixture was cooled to rt, and waterwas added and the product was extracted with heptane. The organic phasewas dried and evaporated. The product was recrystallized fromisopropoanol to get compound J-21.

¹H NMR (400 MHz, CDCl₃) δ 8.03 (d, 2H), 7.27 (d, 2H), 2.60 (s, 6H), 1.49(s, 24H).

Example 30 Synthesis of Intermediate (J-22)

Intermediate J-22 was synthesized from compound J-4 and J-21 accordingto compound J-14 described in example 21.

¹H NMR (300 MHz, DMSO-D₆) δ 8.41 (s, 2H), 8.29 (s, 2H), 8.18 and 8.09 (2s (rotamers), 2H), 7.40 (d, 2H), 7.12 (d, 2H), 4.40 (q, 4H), 2.10 (s,6H), 1.37 (t, 6H).

Example 31 Synthesis of Intermediate (J-23)

Intermediate J-23 was synthesized from compound J-22 according tocompound J-15 described in example 22.

¹H NMR (300 MHz, DMSO-D₆) δ 8.40 (s, 2H), 8.21 (s, 2H), 8.08 (s, 2H),7.39 (d, 2H), 7.13 (d, 2H), 2.12 (s, 6H).

Example 32 Synthesis of Intermediate (J-24)

Intermediate J-24 was synthesized from compound J-23 according tocompound J-16 described in example 23.

¹H NMR (300 MHz, DMSO-D₆) δ 8.25 (s, 2H), 8.09 and 8.00 (2 s (rotamers),2H), 7.94 (d, 2H), 7.57 (d, 2H), 7.37 (d, 2H), 7.13 (d, 2H), 2.12 (s,6H).

Example 33 Synthesis of Intermediate (J-25)

Intermediate J-25 was synthesized from compound J-24 according tocompound J-17 described in example 24.

¹H NMR (400 MHz, DMSO-D₆) δ 9.23 (s, 2H), 9.02 (d, 2H), 8.16 (s, 2H),7.99 (d, 2H), 7.81 (d, 2H), 7.52 (d, 2H), 4.24 (s, 4H).

Example 34 Synthesis of Intermediate (J-26)

Intermediate J-26 was synthesized from compound J-25 according tocompound J-18 described in example 25.

¹H NMR (300 MHz, CDCl₃) δ 8.89 (d, 2H), 8.87 (s, 2H), 7.86 (s, 2H), 7.73(d, 2H), 7.50 (d, 2H), 7.42 (d,2H), 2.19-2.11 (br, 8H), 1.35-0-95 (m,104H), 0.89 (t, 12H), 0.75-0.60 (br, 8H).

Example 35 Synthesis of Intermediate (J-27)

Intermediate J-27 was synthesized from compound J-26 according tocompound J-19 described in example 26.

¹H NMR (300 MHz, CDCl₃) δ 8.89 (d, 2H), 8.87 (s, 2H), 7.85 (s, 2H), 7.73(d, 2H), 7.51 (s, 2H), 2.19-2.11 (br, 8H), 1.50-1.00 (m, 104H), 0.90 (t,12H), 0.73-0.62 (br, 8H), 0.49 (t, 18H).

Example 36 Synthesis of Polymer (P-10)

Polymer P-10 was synthesized from 0.274 mmol (449 mg) of compound J-27and 0.274 mmol (80.5 mg) of 4,7-dibromo-benzo[c]-1,2,5-thiadiazole[15155-41-6], according to polymer P-9 described in example 27. Soxhletextraction gave 79mg polymer P-10 from hexane fraction (GPC data(trichlorobenzene, 150° C.): Mw 27′139, PDI 2.23) and 257 mg polymerP-10 from toluene fraction (GPC data (trichlorobenzene, 150° C.): Mw78′162, PDI 2.28).

Example 37 Synthesis of Polymer P-11 (Same Structure as Polymer P-1Above) Via Direct Heteroarylation Polymerization

0.032 mmol (40 mg) of compound J-9 and 0.032 mmol (12 mg) of4,7-dibromo-benzo[c]-1,2,5-thiadiazole [15155-41-6] were placed togetherwith 10% Pd(Herrmann) catalyst and 15%tri(ortho-methoxy-phenyl)phosphine, 2 equivalents of pivalic acid, 3equivalents of potassiumcarbonate and 2 ml dimethylacetamide in a vialand degassed with argon. Then the reaction mixture was heated andstirred vigorously for 48 hours at 140° C. The polymer P-11 wasprecipitated with water, filtered and washed with water. Then thepolymer was purified and fractionated in analogy to experiments 12-19described above. The chloroform fraction gave a polymer P-11 with thefollowing GPC data (chlorobenzene at 80° C.): Mw 52′300, PDI 1.41.

Application Examples A-1 to -4

Fabrication and electrical characterization of organic field-effecttransistors (OFET) based on the polymers P-1, P-2, P-3, and P-4

The polymers are dissolved at a concentration of 0.75 wt % indichlorobenzene. Back-contact, Top-gate FETs are fabricated from eachformulation according to the following procedure: A PEN-substrate withlithographically pre-patterned gold contacts, serving as source anddrain contact of the FET are used as substrates. 100 μl of theformulation is coated by a standard blade coater yielding a homogenouslayer of the semiconductor over the entire substrate. After the coatingis completed, the substrate is immediately transferred onto a preheatedhotplate and heated for 30 s at 90° C. Next the gate dielectric layerconsisting of Polystyrene 4 wt % dissolved in PGMEA is spin-coated ontop of the organic semiconductor (2500 rpm, 30 s). After spin-coating ofthe dielectric, the substrate is again transferred to the hotplate andannealed for another 5 Min at 90° C. The thickness of the dielectriclayer is 420 nm measured by profilometer. Finally 50 nm thick,shadow-mask patterned gold gate electrodes are deposited by vacuumevaporation to complete FETs in the BCTG-configuration.

The mobility μ is calculated from the root representation of thetransfer characteristic curve (solid grey curve) in the saturationregion. The slope m is determined from the dashed black line in therespective transfer characteristics. The dashed black line is fitted toa region of the square root representation of the drain current ID suchthat a good correlation to the linear slope of the root representationis obtained.

The threshold voltage U_(Th) can be taken from the intersection of blackdashed line with the X-axis portion (V_(GS)).

In order to calculate the electrical properties of the OFET, thefollowing equations are employed:

$\begin{matrix}{\mu = \frac{m^{2}*2L}{C_{G}*W}}\end{matrix}\mspace{14mu} \begin{matrix}{C_{G} = {ɛ_{0}*ɛ_{r}\frac{1}{d}}}\end{matrix}\mspace{11mu} \begin{matrix}{U_{Th} = {{- 1}*\frac{m}{b}}}\end{matrix}\mspace{11mu} \begin{matrix}{{{ON}/{OFF}} = \frac{I_{D}\max}{I_{D}\min}}\end{matrix}$

where ϵ₀ is the vacuum permittivity of 8.85×10⁻¹² As/Vm. ϵ_(r)=2,6 forPolystyrene and d is the thickness of the dielectric. The width overlength ratio W/L is 10.

FIG. 1 show representative transfer characteristics of an FET fabricatedfrom polymer P-1 with V_(GS)=30 V to −30 V at 0.5 V step size withV_(DS)=−30 V. Drain current (black solid curve), Gate current (dottedgrey curve), Square root of drain current (grey solid curve), and fittedslope of square root (dashed black curve).

FIG. 2 show representative transfer characteristics of an FET fabricatedfrom polymer P-2 with V_(GS)=30 V to −30 V at 0.5 V step size withV_(DS)=−30 V. Drain current (black solid curve), Gate current (dottedgrey curve), Square root of drain current (grey solid curve), and fittedslope of square root (dashed black curve).

FIG. 3 show representative transfer characteristics of an FET fabricatedfrom polymer P-3 with V_(GS)=30 V to −30 V at 0.5 V step size withV_(DS)=−30 V. Drain current (black solid curve), Gate current (dottedgrey curve), Square root of drain current (grey solid curve), and fittedslope of square root (dashed black curve).

FIG. 4 show representative transfer characteristics of an FET fabricatedfrom polymer P-4 with V_(GS)=30 V to −30 V at 0.5 V step size withV_(DS)=−30 V. Drain current (black solid curve), Gate current (dottedgrey curve), Square root of drain current (grey solid curve), and fittedslope of square root (dashed black curve).

The following mobilities, threshold voltages and ON/OFF ratios are theaverage values obtained for the respective compound. The number of TFTsentering the calculation of the average is given in the table:

Number Field-effect mobility Threshold volt- ON/OFF Compound of TFTs μ[cm²/Vs] age U_(TH) [V] ratio P-1 20 2.0 −11 4E6 P-2 19 1.4 −8.5 4E6 P-318 1.4 −10.7 2E6 P-4 13 7E−4 −8.9 8E2

1-17. (canceled) 18: A polymer, comprising at least one unit of formulae:

wherein: X, Y are S; Q is C; L¹ and L² are independently from each other and at each occurrence selected from the group consisting of C₆₋₃₀-arylene, 5 to 30 membered heteroarylene,

C₆₋₃₀-arylene and 5 to 30 membered heteroarylene can be substituted with one to six substituents R³ at each occurrence selected from the group consisting of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, OR³¹, OC(O)—R³¹, C(O)—OR³¹, C(O)—R³¹, NR³¹R³², NR³¹—C(O)R³², C(O)—NR³¹R³², N[C(O)R³¹][C(O)R³²], SR³¹, halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and OH,

can be substituted with one or two substituents R⁴ at each occurrence selected from the group consisting of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, C(O)—R⁴¹, C(O)—NR⁴¹R⁴², C(O)—OR⁴¹ and CN, R³¹, R³², R⁴¹ and R⁴² are independently from each other and at each occurrence selected from the group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be substituted with one to ten substituents independently selected from the group consisting of C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and at least two CH₂-groups, but not adjacent CH₂-groups of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be replaced by O or S, C₅₋₁₂-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and one or two CH₂-groups, but not adjacent CH₂-groups, of C₅₋₁₂-cycloalkyl can be replaced by O, S, OC(O), CO, NR^(i) or NR^(i)—CO, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂, R^(Siv), R^(Siw), R^(Six) are independently from each other selected from the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₆-cycloalkyl, phenyl and O—Si(CH₃)₃, R^(i) and R^(j) are independently selected from the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₀-aryl, and 5 to 14 membered heteroaryl, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be substituted with one to five substituents selected from the group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂, C₅₋₈-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)-C(O)R^(l), C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂, R^(k) and R^(l) are independently selected from the group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO₂, R², R^(2′) and R^(2″) are at each occurrence selected from the group consisting of hydrogen, unsubstituted C₁₋₃₀-alkyl and halogen, R is at each occurrence unsubstituted C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl, or C₃₋₅₀-alkynyl, m is 0, 1, 2, 3 or 4, and p is 2 to
 1000. 19: The polymers according to claim 18, wherein: R², R^(2′) and R^(2″) are at each occurrence hydrogen, and R is at each occurrence C₁₋₃₆-alkyl. 20: The polymers of claim 18, wherein: L¹and L² are independently from each other and at each occurrence selected from the group consisting of C₆₋₃₀-arylene and 5 to 30 membered heteroarylene, and

C₆₋₃₀-arylene and 5 to 30 membered heteroarylene can be substituted with one to six substituents R³ at each occurrence selected from the group consisting of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, OR³¹, OC(O)—R³¹, C(O)—OR³¹, C(O)—R³¹, NR³¹R³², NR³¹—C(O)R³², C(O)—NR³¹R³², SR³¹, halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and OH,

can be substituted with one or two substituents R⁴ at each occurrence selected from the group consisting of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, C(O)—R⁴¹, C(O)—NR^(4l)R⁴², C(O)—OR⁴¹ and CN, R³¹, R³², R⁴¹ and R⁴² are independently from each other and at each occurrence selected from the group consisting of H, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl, C₂₋₃₀-alkynyl, C₅₋₁₂-cycloalkyl, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl, C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be substituted with one to ten substituents independently selected from the group consisting of C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and at least two CH₂-groups, but not adjacent CH₂-groups of C₁₋₃₀-alkyl, C₂₋₃₀-alkenyl and C₂₋₃₀-alkynyl can be replaced by O or S, C₅₋₁₂-cycloalkyl can be substituted with one to six substituents independently selected from the group consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R^(i)][C(O)R^(j)], SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂; and one or two CH₂-groups, but not adjacent CH₂-groups, of C₅₋₁₂-cycloalkyl can be replaced by O, S, OC(O), CO, NR^(i) or NR^(i)—CO, C₆₋₁₈-aryl and 5 to 20 membered heteroaryl can be substituted with one to six substituents independently selected from the group consisting of C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, 5 to 14 membered heteroaryl, OR^(i), OC(O)—R^(j), C(O)—OR^(i), C(O)—R^(i), NR^(i)R^(j), NR^(i)—C(O)R^(j), C(O)—NR^(i)R^(j), N[C(O)R][C(O)R^(j)], SR^(i), halogen, CN, SiR^(Siv)R^(Siw)R^(Six) and NO₂, R^(Siv), R^(Siw), R^(Six) are independently from each other selected from the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, phenyl and O—Si(CH₃)₃, R^(i) and R^(j) are independently selected from the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be substituted with one to five substituents selected from the group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂, C₅₋₈-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(k), OC(O)—R^(l), C(O)—OR^(k), C(O)—R^(k), NR^(k)R^(l), NR^(k)—C(O)R^(l), C(O)—NR^(k)R^(l), N[C(O)R^(k)][C(O)R^(l)], SR^(k), halogen, CN, and NO₂, R^(k) and R^(l) are independently selected from the group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl, and C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO₂. 21: The polymer of claim 20, wherein: L¹ and L² are independently from each other and at each occurrence selected from the group consisting of C₆₋₃₀-arylene and 5 to 30 membered heteroarylene and

C₆₋₃₀-arylene and 5 to 30 membered heteroarylene is selected from the group consisting of

R¹⁰⁴ and R¹⁰⁵ are independently and at each occurrence selected from the group consisting of H, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl, C₂₋₂₀-alkynyl, C₅₋₈-cycloalkyl, C₆₋₁₄-aryl, and 5 to 14 membered heteroaryl, or R¹⁰⁴ and R¹⁰⁵, if attached to the same atom, together with the atom, to which they are attached, form a 5 to 12 membered ring system, C₁₋₂₀-alkyl, C₂₋₂₀-alkenyl and C₂₋₂₀-alkynyl can be substituted with one to five substituents selected from the group consisting of C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂, C₅₋₈-cycloalkyl can be substituted with one to five substituents selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂, C₆₋₁₄-aryl and 5 to 14 membered heteroaryl can be substituted with one to five substituents independently selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂, 5 to 12 membered ring system can be substituted with one to five substituents selected from the group consisting of C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl, C₂₋₁₀-alkynyl, C₅₋₆-cycloalkyl, C₆₋₁₀-aryl, 5 to 10 membered heteroaryl, OR^(s), OC(O)—R^(t), C(O)—OR^(s), C(O)—R^(s), NR^(s)R^(t), NR^(s)—C(O)R^(t), C(O)—NR^(s)R^(t), N[C(O)R^(s)][C(O)R^(t)], SR^(s), halogen, CN, and NO₂, R^(s) and R^(t) are independently selected from the group consisting of H, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl, C₁₋₁₀-alkyl, C₂₋₁₀-alkenyl and C₂₋₁₀-alkynyl can be substituted with one to five substituents selected from the group consisting of halogen, CN and NO₂, C₆₋₃₀-arylene and 5 to 30 membered heteroarylene can be substituted with one to six substituents R³ at each occurrence selected from the group consisting of C₁₋₃₀-alkyl and halogen,

can be substituted with one or two substituents R⁴ at each occurrence selected from the group consisting of C₁₋₃₀-alkyl, C(O)—R⁴¹, C(O)—OR⁴¹ and CN, R⁴¹ is at each occurrence C₁₋₃₀-alkyl, and X′ is S. 22: The polymer of claim 21, wherein: L¹ and L² are independently from each other selected from a group consisting of

and X′ is S. 23: The polymer of claim 22, wherein L¹ and L² are selected from the group consisting of

24: The polymer of claim 18, wherein m is 0, 1 or
 2. 25: A process for preparing the polymer of claim 18, the process comprising reacting a compound of one of formulae (3a)-(3g):

with a compound of formula (10):

wherein Z* is at each occurrence I, Br, Cl, O—S(O)₂CF₃ or H, Z^(a) and Z^(b) are independently selected from the group consisting of B(OZ¹)(OZ²), SnZ¹Z²Z³,

Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶ are independently from each other and at each occurrence H or C₁₋₄-alkyl, and Z^(a) and Z^(b) are Br if Z* is H. 26: A compound of one of formulae (3a)-(3g):

wherein: X, Y are S; Q is C; R², R^(2′) and R^(2″) are at each occurrence selected from the group consisting of hydrogen, unsubstituted C₁₋₃₀-alkyl and halogen, and R is at each occurrence unsubstituted C₁₋₅₀-alkyl, C₃₋₅₀-alkenyl, or C₃₋₅₀-alkynyl. 27: An electronic device, comprising the polymer of claim
 18. 28: The electronic device of claim 27, wherein the electronic device is an organic field effect transistor. 